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

HRID 1374315Notes

Reaction equation

HRID 1374315 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][C@@H:8]1[CH2:13][CH2:12][C@H:11]([NH:14]C(OCC2C=CC=CC=2)=O)[C@H:10]([CH2:25][O:26][CH3:27])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>CO.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6](=[O:28])[NH:7][C@@H:8]1[CH2:13][CH2:12][C@H:11]([NH2:14])[C@H:10]([CH2:25][O:26][CH3:27])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

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 99.8%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of (1R,3R,4S)-(4-benzyloxycarbonylamino-3-methoxymethylcyclohexyl)carbamic acid tert-butyl ester (1.24 g) was dissolved in MeOH (20 mL) and the resultant solution was charged with 20 wt % Pd(OH)2/C (300 mg) before being evacuated and purged with hydrogen. The reaction was stirred under 1 atm of H2 for 3 h and then filtered through celite with EtOAc washings. The filtrate was concentrated in vacuo to provide (1R,3R,4S)-(4-amino-3-methoxymethyl-cyclohexyl)-carbamic acid tert-butyl ester (815 mg). MS found: (M+H)+=259.2.

Workup

  1. custombefore being evacuated
  2. custompurged with hydrogen
  3. filtrationfiltered through celite with EtOAc washings
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-4e483e8d87094555bf5542eb1719ece9
Source dataset
uspto-grants-2007_01
Patent number
US07163937B2

Reaction notes

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