tert-butyl (1R,3R,4S)-4-benzyloxycarbonylamino-3-(methoxymethyl)cyclohexylcarbamate → tert-butyl (1R,3R,4S)-4-amino-3-(methoxymethyl)cyclohexylcarbamate

HRID 2225245Notes

Reaction equation

HRID 2225245 reaction equation
C(OC([NH:11][C@H:12]1[CH2:17][CH2:16][C@@H:15]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:14][C@H:13]1[CH2:26][O:27][CH3:28])=O)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[NH2:11][C@H:12]1[CH2:17][CH2:16][C@@H:15]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:14][C@H:13]1[CH2:26][O:27][CH3:28]

Participants

4

Reactant 1

HCID 68766937tert-butyl (1R,3R,4S)-4-benzyloxycarbonylamino-3-(methoxymethyl)cyclohexylcarbamate

Product 1

HCID 68765639tert-butyl (1R,3R,4S)-4-amino-3-(methoxymethyl)cyclohexylcarbamateYield 106.9%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of tert-butyl (1R,3R,4S)-4-benzyloxycarbonylamino-3-(methoxymethyl)cyclohexylcarbamate (64 mg, 0.163 mmol) in methanol (3 mL) was stirred with Pearlman's catalyst (20% Pd(OH)2 on charcoal, 65 mg) under hydrogen at atmospheric pressure and rt for 22 h. The mixture was filtered through Celite and the solids were washed with methanol. The filtrate was concentrated to provide tert-butyl (1R,3R,4S)-4-amino-3-(methoxymethyl)cyclohexylcarbamate as a pale yellow glassy foam (45 mg) which was used without further purification. MS found: (M+H)+=259.2.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washthe solids were washed with methanol
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-87efa1480a0847f48e09808cabe17bae
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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