361442-04-8Relevant articles and documents
Racemisation of (R)-N-Boc-3-hydroxyadamant-1-yl glycine
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, (2011/10/12)
The present invention refers to the preparation of racemic N-Boc-3-hydroxyadamant-1-yl glycine.
Version: 1.0
Creation Date: Aug 14, 2017
Revision Date: Aug 14, 2017
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More Details:361442-04-8 SDS
(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-1-oxoethyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile
Conditions | Yield |
---|---|
With sodium hydroxide In dichloromethane; water at 20℃; for 1h; pH=9; |
(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-1-oxoethyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile
Conditions | Yield |
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Multi-step reaction with 3 steps 1.1: 4-methyl-morpholine / ethyl acetate; acetic acid butyl ester / 0.08 h / 0 °C / Inert atmosphere 1.2: .(R).T3P / 17.5 h / 0 - 25 °C 2.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 1.5 h / 0 °C 2.2: 20 - 25 °C / pH > 10 3.1: hydrogenchloride; water / dichloromethane; methanol / 20.67 h / 0 - 20 °C 3.2: pH > 11 View Scheme |
(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-1-oxoethyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile
Conditions | Yield |
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Multi-step reaction with 2 steps 1.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 1.5 h / 0 °C 1.2: 20 - 25 °C / pH > 10 2.1: hydrogenchloride; water / dichloromethane; methanol / 20.67 h / 0 - 20 °C 2.2: pH > 11 View Scheme |
(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-1-oxoethyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile
Conditions | Yield |
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Multi-step reaction with 3 steps 1.1: 4-methyl-morpholine / ethyl acetate; acetic acid butyl ester / 0.08 h / 0 °C / Inert atmosphere 1.2: .(R).T3P / 17.5 h / 0 - 25 °C 2.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 1.5 h / 0 °C 2.2: 20 - 25 °C / pH > 10 3.1: hydrogenchloride; water / dichloromethane; methanol / 20.67 h / 0 - 20 °C 3.2: pH > 11 View Scheme |
(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-1-oxoethyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile
Conditions | Yield |
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Stage #1: [(1S)-2-[(1S,3S,5S)-3-cyano-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-2-oxoethyl]carbamic acid-1,1-dimethylethyl ester With hydrogenchloride; water In methanol; dichloromethane at 0 - 20℃; for 20.6667h; Stage #2: With sodium hydroxide In water pH=> 11; |
(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-1-oxoethyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile
Conditions | Yield |
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Multi-step reaction with 4 steps 1.1: 1,1'-carbonyldiimidazole / dimethyl sulfoxide / 4.5 h / 20 - 25 °C 1.2: 38 h / 20 - 25 °C 1.3: 0.67 h 2.1: 4-methyl-morpholine / ethyl acetate; acetic acid butyl ester / 0.08 h / 0 °C / Inert atmosphere 2.2: .(R).T3P / 17.5 h / 0 - 25 °C 3.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 1.5 h / 0 °C 3.2: 20 - 25 °C / pH > 10 4.1: hydrogenchloride; water / dichloromethane; methanol / 20.67 h / 0 - 20 °C 4.2: pH > 11 View Scheme |
(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-1-oxoethyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile
Conditions | Yield |
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Multi-step reaction with 5 steps 1.1: (1R,2S)-2-Amino-1,2-diphenylethanol / ethyl acetate / 3.33 h / 70 °C 2.1: hydrogenchloride; water / ethyl acetate; water / pH 3 3.1: 4-methyl-morpholine / ethyl acetate; acetic acid butyl ester / 0.08 h / 0 °C / Inert atmosphere 3.2: .(R).T3P / 17.5 h / 0 - 25 °C 4.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 1.5 h / 0 °C 4.2: 20 - 25 °C / pH > 10 5.1: hydrogenchloride; water / dichloromethane; methanol / 20.67 h / 0 - 20 °C 5.2: pH > 11 View Scheme | |
Multi-step reaction with 6 steps 1.1: (1R,2S)-2-Amino-1,2-diphenylethanol / ethyl acetate / 3.33 h / 70 °C 2.1: hydrogenchloride; water / ethyl acetate; water / pH 3 3.1: 1,1'-carbonyldiimidazole / dimethyl sulfoxide / 4.5 h / 20 - 25 °C 3.2: 38 h / 20 - 25 °C 3.3: 0.67 h 4.1: 4-methyl-morpholine / ethyl acetate; acetic acid butyl ester / 0.08 h / 0 °C / Inert atmosphere 4.2: .(R).T3P / 17.5 h / 0 - 25 °C 5.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 1.5 h / 0 °C 5.2: 20 - 25 °C / pH > 10 6.1: hydrogenchloride; water / dichloromethane; methanol / 20.67 h / 0 - 20 °C 6.2: pH > 11 View Scheme |
(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-1-oxoethyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: hydrogenchloride; water / ethyl acetate; water / pH 3 2.1: 4-methyl-morpholine / ethyl acetate; acetic acid butyl ester / 0.08 h / 0 °C / Inert atmosphere 2.2: .(R).T3P / 17.5 h / 0 - 25 °C 3.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 1.5 h / 0 °C 3.2: 20 - 25 °C / pH > 10 4.1: hydrogenchloride; water / dichloromethane; methanol / 20.67 h / 0 - 20 °C 4.2: pH > 11 View Scheme |
(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-1-oxoethyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: hydrogenchloride; water / ethyl acetate; water / pH 3 2.1: 1,1'-carbonyldiimidazole / dimethyl sulfoxide / 4.5 h / 20 - 25 °C 2.2: 38 h / 20 - 25 °C 2.3: 0.67 h 3.1: 4-methyl-morpholine / ethyl acetate; acetic acid butyl ester / 0.08 h / 0 °C / Inert atmosphere 3.2: .(R).T3P / 17.5 h / 0 - 25 °C 4.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 1.5 h / 0 °C 4.2: 20 - 25 °C / pH > 10 5.1: hydrogenchloride; water / dichloromethane; methanol / 20.67 h / 0 - 20 °C 5.2: pH > 11 View Scheme |
The present invention refers to the preparation of racemic N-Boc-3-hydroxyadamant-1-yl glycine.