3-Nitrobenzaldehyde → tert-Butyl (1R,4R)-4-(3-nitrobenzylamino)cyclohexylcarbamate

HRID 1054025Notes

Reaction equation

[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:3]1.[N+:16]([C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH:22]=O)([O-:18])=[O:17].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO>[N+:16]([C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22][NH:1][CH:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:4][CH2:3]1)([O-:18])=[O:17]

Participants

Conditions

Temperature: 30 °C

Procedure

To a solution of tert-butyl N-(4-aminocyclohexyl)carbamate (25 g, 117 mmol, 1.0 eq) and 3-nitrobenzaldehyde (18 g, 117 mmol, 1.0 eq) in MeOH (500 mL) was added NaBH(OAc)3 (50 g, 234 mmol, 2.0 eq) by portions. Then the resulting mixture was stirred overnight at 30° C. LC-MS indicated complete conversion. The solvent was removed under vacuum and the residue was purified by column chromatography (DCM:MeOH=15:1) to provide tert-butyl N-(4-[(3-nitrobenzyl)amino]cyclohexyl)carbamate (33 g, 83%) as a yellow solid.

Workup

customThe solvent was removed under vacuum
customthe residue was purified by column chromatography (DCM:MeOH=15:1)

Sources & evidence

ORD record: ord-d0cf2deaa2a84c299e2dd2a628d00bf3
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394286B2

Reaction notes

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