(+/-)-tert-butyl (1R,5S,65)-6-(2-cyanoethoxy)-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enylcarbamate → tert-butyl ((1S,2R,3R,5S)-5-(3-aminopyridin-4-yl)-2-(2-cyanoethoxy)-3-methylcyclohexyl)carbamate
Reaction equation
[C:1]([CH2:3][CH2:4][O:5][C@@H:6]1[C@H:11]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:10]=[C:9]([C:20]2[CH:25]=[CH:24][N:23]=[CH:22][C:21]=2[N+:26]([O-])=O)[CH2:8][C@@H:7]1[CH3:29])#[N:2]>CCO>[NH2:26][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][C:20]=1[C@@H:9]1[CH2:10][C@H:11]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C@H:6]([O:5][CH2:4][CH2:3][C:1]#[N:2])[C@H:7]([CH3:29])[CH2:8]1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
Method 6 was followed using (+/−)-tert-butyl (1R,5S,65)-6-(2-cyanoethoxy)-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enylcarbamate with SFC (15% EtOH, 100 mL/min, OJ column) to yield tert-butyl ((1S,2R,3R,5S)-5-(3-aminopyridin-4-yl)-2-(2-cyanoethoxy)-3-methylcyclohexyl)carbamate (31% yield, 99% ee) and tert-butyl ((1R,2S,3S,5R)-5-(3-aminopyridin-4-yl)-2-(2-cyanoethoxy)-3-methylcyclohexyl) carbamate (26% yield, 99% ee). LC/MS (m/z)=375.3 (MH+), Rt=0.65 min.
Sources & evidence
- ORD record
- ord-e96cadf02a7643ac9c7a72852f8e2982
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09173883B2
Reaction notes
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