(+/-)-tert-butyl (1R,5S,6S)-6-ethoxy-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enylcarbamate → tert-butyl ((1S,2R,3R,5S)-5-(3-aminopyridin-4-yl)-2-ethoxy-3-methylcyclohexyl)carbamate

HRID 879209Notes

Reaction equation

HRID 879209 reaction equation
[CH2:1]([O:3][C@@H:4]1[C@H:9]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:8]=[C:7]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][C:19]=2[N+:24]([O-])=O)[CH2:6][C@@H:5]1[CH3:27])[CH3:2]>CCCCCCC.CCO>[NH2:24][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][C:18]=1[C@@H:7]1[CH2:8][C@H:9]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[C@H:4]([O:3][CH2:1][CH3:2])[C@H:5]([CH3:27])[CH2:6]1.[NH2:24][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][C:18]=1[C@H:7]1[CH2:8][C@@H:9]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[C@@H:4]([O:3][CH2:1][CH3:2])[C@@H:5]([CH3:27])[CH2:6]1

Participants

4

Reactant 1

HCID 86705257(+/-)-tert-butyl (1R,5S,6S)-6-ethoxy-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enylcarbamate

Product 2

HCID 86705258tert-butyl ((1S,2R,3R,5S)-5-(3-aminopyridin-4-yl)-2-ethoxy-3-methylcyclohexyl)carbamateYield 33%HCID 86705259tert-butyl ((1R,2S,3S,5R)-5-(3-aminopyridin-4-yl)-2-ethoxy-3-methylcyclohexyl)carbamateYield 28%

Reagents, catalysts & solvents 1

HCID 22502148Ethanol heptaneSolvent

Procedure

Method 6 was followed using (+/−)-tert-butyl (1R,5S,6S)-6-ethoxy-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enylcarbamate with Chiral HPLC (Heptane/EtOH=90/10, 20 mL/min, IC column) to yield tert-butyl ((1S,2R,3R,5S)-5-(3-aminopyridin-4-yl)-2-ethoxy-3-methylcyclohexyl)carbamate (33% yield, 99% ee) and tert-butyl ((1R,2S,3S,5R)-5-(3-aminopyridin-4-yl)-2-ethoxy-3-methylcyclohexyl)carbamate (28% yield, 99% ee). LC/MS (m/z)=350.2 (MH+), Rt=0.72 min.

Sources & evidence

ORD record
ord-762e7b8dc9234317ac314f4ae9d92262
Source dataset
uspto-grants-2015_03
Patent number
US08987457B2

Reaction notes

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