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David A Griffith - One of the best experts on this subject based on the ideXlab platform.
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the synthesis of methyl substituted spirocyclic piperidine azetidine 2 7 diazaspiro 3 5 nonane and spirocyclic piperidine pyrrolidine 2 8 diazaspiro 4 5 decane ring systems
Journal of Organic Chemistry, 2016Co-Authors: Aaron Smith, Shawn Cabral, Daniel W Kung, Colin R Rose, James Alfred Southers Jr., Carmen N Garciairizarry, David B Damon, Scott W Bagley, David A GriffithAbstract:The synthesis of a series of pharmaceutically important N-protected methyl-substituted spirocyclic piperidine-azetidine (2,7-diazaspiro[3.5]nonane) and spirocyclic piperidine-pyrrolidine (2,8-diazaspiro[4.5]decane) ring systems was developed. These motifs contain two differentiated sites (protected secondary amines) to allow for further functionalization via reductive Amination, amidation, or other chemistry. The methyl-substituted spiroazetidine ring systems were accessed using nitrile lithiation/alkylation chemistry while the methyl-substituted spiropyrrolidines were synthesized by 1,4-addition reactions with nitroalkanes, followed by reduction and cyclization. These conditions were then scaled for the synthesis of 1-methyl spirocyclic piperidine-pyrrolidine with a classical resolution of the product using a tartaric acid derivative to isolate a single enantiomer.
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The Synthesis of Methyl-Substituted Spirocyclic Piperidine-Azetidine (2,7-Diazaspiro[3.5]nonane) and Spirocyclic Piperidine-Pyrrolidine (2,8-Diazaspiro[4.5]decane) Ring Systems
2016Co-Authors: Aaron C. Smith, Shawn Cabral, Colin R Rose, David B Damon, Daniel W. Kung, James A. Southers, Carmen N. García-irizarry, Scott W. Bagley, David A GriffithAbstract:The synthesis of a series of pharmaceutically important N-protected methyl-substituted spirocyclic piperidine-azetidine (2,7-diazaspiro[3.5]nonane) and spirocyclic piperidine-pyrrolidine (2,8-diazaspiro[4.5]decane) ring systems was developed. These motifs contain two differentiated sites (protected secondary amines) to allow for further functionalization via reductive Amination, amidation, or other chemistry. The methyl-substituted spiroazetidine ring systems were accessed using nitrile lithiation/alkylation chemistry while the methyl-substituted spiropyrrolidines were synthesized by 1,4-addition reactions with nitroalkanes, followed by reduction and cyclization. These conditions were then scaled for the synthesis of 1-methyl spirocyclic piperidine-pyrrolidine with a classical resolution of the product using a tartaric acid derivative to isolate a single enantiomer
Aaron Smith - One of the best experts on this subject based on the ideXlab platform.
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the synthesis of methyl substituted spirocyclic piperidine azetidine 2 7 diazaspiro 3 5 nonane and spirocyclic piperidine pyrrolidine 2 8 diazaspiro 4 5 decane ring systems
Journal of Organic Chemistry, 2016Co-Authors: Aaron Smith, Shawn Cabral, Daniel W Kung, Colin R Rose, James Alfred Southers Jr., Carmen N Garciairizarry, David B Damon, Scott W Bagley, David A GriffithAbstract:The synthesis of a series of pharmaceutically important N-protected methyl-substituted spirocyclic piperidine-azetidine (2,7-diazaspiro[3.5]nonane) and spirocyclic piperidine-pyrrolidine (2,8-diazaspiro[4.5]decane) ring systems was developed. These motifs contain two differentiated sites (protected secondary amines) to allow for further functionalization via reductive Amination, amidation, or other chemistry. The methyl-substituted spiroazetidine ring systems were accessed using nitrile lithiation/alkylation chemistry while the methyl-substituted spiropyrrolidines were synthesized by 1,4-addition reactions with nitroalkanes, followed by reduction and cyclization. These conditions were then scaled for the synthesis of 1-methyl spirocyclic piperidine-pyrrolidine with a classical resolution of the product using a tartaric acid derivative to isolate a single enantiomer.
David B Damon - One of the best experts on this subject based on the ideXlab platform.
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the synthesis of methyl substituted spirocyclic piperidine azetidine 2 7 diazaspiro 3 5 nonane and spirocyclic piperidine pyrrolidine 2 8 diazaspiro 4 5 decane ring systems
Journal of Organic Chemistry, 2016Co-Authors: Aaron Smith, Shawn Cabral, Daniel W Kung, Colin R Rose, James Alfred Southers Jr., Carmen N Garciairizarry, David B Damon, Scott W Bagley, David A GriffithAbstract:The synthesis of a series of pharmaceutically important N-protected methyl-substituted spirocyclic piperidine-azetidine (2,7-diazaspiro[3.5]nonane) and spirocyclic piperidine-pyrrolidine (2,8-diazaspiro[4.5]decane) ring systems was developed. These motifs contain two differentiated sites (protected secondary amines) to allow for further functionalization via reductive Amination, amidation, or other chemistry. The methyl-substituted spiroazetidine ring systems were accessed using nitrile lithiation/alkylation chemistry while the methyl-substituted spiropyrrolidines were synthesized by 1,4-addition reactions with nitroalkanes, followed by reduction and cyclization. These conditions were then scaled for the synthesis of 1-methyl spirocyclic piperidine-pyrrolidine with a classical resolution of the product using a tartaric acid derivative to isolate a single enantiomer.
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The Synthesis of Methyl-Substituted Spirocyclic Piperidine-Azetidine (2,7-Diazaspiro[3.5]nonane) and Spirocyclic Piperidine-Pyrrolidine (2,8-Diazaspiro[4.5]decane) Ring Systems
2016Co-Authors: Aaron C. Smith, Shawn Cabral, Colin R Rose, David B Damon, Daniel W. Kung, James A. Southers, Carmen N. García-irizarry, Scott W. Bagley, David A GriffithAbstract:The synthesis of a series of pharmaceutically important N-protected methyl-substituted spirocyclic piperidine-azetidine (2,7-diazaspiro[3.5]nonane) and spirocyclic piperidine-pyrrolidine (2,8-diazaspiro[4.5]decane) ring systems was developed. These motifs contain two differentiated sites (protected secondary amines) to allow for further functionalization via reductive Amination, amidation, or other chemistry. The methyl-substituted spiroazetidine ring systems were accessed using nitrile lithiation/alkylation chemistry while the methyl-substituted spiropyrrolidines were synthesized by 1,4-addition reactions with nitroalkanes, followed by reduction and cyclization. These conditions were then scaled for the synthesis of 1-methyl spirocyclic piperidine-pyrrolidine with a classical resolution of the product using a tartaric acid derivative to isolate a single enantiomer
Colin R Rose - One of the best experts on this subject based on the ideXlab platform.
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the synthesis of methyl substituted spirocyclic piperidine azetidine 2 7 diazaspiro 3 5 nonane and spirocyclic piperidine pyrrolidine 2 8 diazaspiro 4 5 decane ring systems
Journal of Organic Chemistry, 2016Co-Authors: Aaron Smith, Shawn Cabral, Daniel W Kung, Colin R Rose, James Alfred Southers Jr., Carmen N Garciairizarry, David B Damon, Scott W Bagley, David A GriffithAbstract:The synthesis of a series of pharmaceutically important N-protected methyl-substituted spirocyclic piperidine-azetidine (2,7-diazaspiro[3.5]nonane) and spirocyclic piperidine-pyrrolidine (2,8-diazaspiro[4.5]decane) ring systems was developed. These motifs contain two differentiated sites (protected secondary amines) to allow for further functionalization via reductive Amination, amidation, or other chemistry. The methyl-substituted spiroazetidine ring systems were accessed using nitrile lithiation/alkylation chemistry while the methyl-substituted spiropyrrolidines were synthesized by 1,4-addition reactions with nitroalkanes, followed by reduction and cyclization. These conditions were then scaled for the synthesis of 1-methyl spirocyclic piperidine-pyrrolidine with a classical resolution of the product using a tartaric acid derivative to isolate a single enantiomer.
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The Synthesis of Methyl-Substituted Spirocyclic Piperidine-Azetidine (2,7-Diazaspiro[3.5]nonane) and Spirocyclic Piperidine-Pyrrolidine (2,8-Diazaspiro[4.5]decane) Ring Systems
2016Co-Authors: Aaron C. Smith, Shawn Cabral, Colin R Rose, David B Damon, Daniel W. Kung, James A. Southers, Carmen N. García-irizarry, Scott W. Bagley, David A GriffithAbstract:The synthesis of a series of pharmaceutically important N-protected methyl-substituted spirocyclic piperidine-azetidine (2,7-diazaspiro[3.5]nonane) and spirocyclic piperidine-pyrrolidine (2,8-diazaspiro[4.5]decane) ring systems was developed. These motifs contain two differentiated sites (protected secondary amines) to allow for further functionalization via reductive Amination, amidation, or other chemistry. The methyl-substituted spiroazetidine ring systems were accessed using nitrile lithiation/alkylation chemistry while the methyl-substituted spiropyrrolidines were synthesized by 1,4-addition reactions with nitroalkanes, followed by reduction and cyclization. These conditions were then scaled for the synthesis of 1-methyl spirocyclic piperidine-pyrrolidine with a classical resolution of the product using a tartaric acid derivative to isolate a single enantiomer
Shawn Cabral - One of the best experts on this subject based on the ideXlab platform.
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the synthesis of methyl substituted spirocyclic piperidine azetidine 2 7 diazaspiro 3 5 nonane and spirocyclic piperidine pyrrolidine 2 8 diazaspiro 4 5 decane ring systems
Journal of Organic Chemistry, 2016Co-Authors: Aaron Smith, Shawn Cabral, Daniel W Kung, Colin R Rose, James Alfred Southers Jr., Carmen N Garciairizarry, David B Damon, Scott W Bagley, David A GriffithAbstract:The synthesis of a series of pharmaceutically important N-protected methyl-substituted spirocyclic piperidine-azetidine (2,7-diazaspiro[3.5]nonane) and spirocyclic piperidine-pyrrolidine (2,8-diazaspiro[4.5]decane) ring systems was developed. These motifs contain two differentiated sites (protected secondary amines) to allow for further functionalization via reductive Amination, amidation, or other chemistry. The methyl-substituted spiroazetidine ring systems were accessed using nitrile lithiation/alkylation chemistry while the methyl-substituted spiropyrrolidines were synthesized by 1,4-addition reactions with nitroalkanes, followed by reduction and cyclization. These conditions were then scaled for the synthesis of 1-methyl spirocyclic piperidine-pyrrolidine with a classical resolution of the product using a tartaric acid derivative to isolate a single enantiomer.
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The Synthesis of Methyl-Substituted Spirocyclic Piperidine-Azetidine (2,7-Diazaspiro[3.5]nonane) and Spirocyclic Piperidine-Pyrrolidine (2,8-Diazaspiro[4.5]decane) Ring Systems
2016Co-Authors: Aaron C. Smith, Shawn Cabral, Colin R Rose, David B Damon, Daniel W. Kung, James A. Southers, Carmen N. García-irizarry, Scott W. Bagley, David A GriffithAbstract:The synthesis of a series of pharmaceutically important N-protected methyl-substituted spirocyclic piperidine-azetidine (2,7-diazaspiro[3.5]nonane) and spirocyclic piperidine-pyrrolidine (2,8-diazaspiro[4.5]decane) ring systems was developed. These motifs contain two differentiated sites (protected secondary amines) to allow for further functionalization via reductive Amination, amidation, or other chemistry. The methyl-substituted spiroazetidine ring systems were accessed using nitrile lithiation/alkylation chemistry while the methyl-substituted spiropyrrolidines were synthesized by 1,4-addition reactions with nitroalkanes, followed by reduction and cyclization. These conditions were then scaled for the synthesis of 1-methyl spirocyclic piperidine-pyrrolidine with a classical resolution of the product using a tartaric acid derivative to isolate a single enantiomer
