HCID 69286629, compound → HCID 86596970, compound

HRID 2225295Notes

Reaction equation

HRID 2225295 reaction equation
[C:1]([C@H:4]1[C@@H:9]([NH:10]C(OCC2C=CC=CC=2)=O)[CH2:8][CH2:7][C@@H:6]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:5]1)(=[O:3])[CH3:2]>CO.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[C:1]([C@H:4]1[C@@H:9]([NH2:10])[CH2:8][CH2:7][C@@H:6]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 69286629HCID 69286629, compound

Product 1

HCID 86596970HCID 86596970, compoundYield 109.2%

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 887MethanolSolvent

Procedure

Tert-butyl (1R,3R,4S)-3-acetyl-4-benzyloxycarbonylaminocyclohexylcarbamate (600 mg) in MeOH (5 mL) was charged with 5% Pd/BaSO4 (300 mg). The reaction flask was evacuated and then back-filled with hydrogen; this was repeated three more times. The reaction was stirred under 1 atm of H2 for 2 h and then filtered and concentrated to provide tert-butyl (1R,3R,4S)-3-acetyl-4-aminocyclohexylcarbamate (430 mg). MS (ES+)=279.2 (M+H)+.

Workup

  1. customThe reaction flask was evacuated
  2. additionback-filled with hydrogen
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8f013d5075fa45dd97c8a3d479e9cbf5
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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