HCID 86596944, compound → HCID 86596945, compound

HRID 2225241Notes

Reaction equation

HRID 2225241 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[C:26]([CH3:28])=[CH2:27])=O)C1C=CC=CC=1>CO.[Pd]>[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[CH:26]([CH3:28])[CH3:27]

Participants

4

Reactant 1

HCID 86596944HCID 86596944, compound

Product 1

HCID 86596945HCID 86596945, compoundYield 107.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of tert-butyl (1R,3S,4S)-4-benzyloxycarbonylamino-3-(prop-1-en-2-yl)cyclohexylcarbamate (1.1 g) in MeOH (10 mL) was charged with 10% Pd/C, Degussa (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 12 h and then filtered and concentrated to provide tert-butyl (1R,3S,4S)-4-amino-3-isopropylcyclohexylcarbamate (780 mg). MS (ES+)=257.3 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-8a2b48e536bf4d949857339a53dcda61
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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