HCID 69286608, compound → HCID 69285468, compound

HRID 2225230Notes

Reaction equation

HRID 2225230 reaction equation
C(OC(=O)[NH:10][C@H:11]1[CH2:16][CH2:15][C@@H:14]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13][C@@H:12]1[CH:25]=[CH:26][CH:27]([CH3:29])[CH3:28])C1C=CC=CC=1>CO.[Pd]>[C:21]([O:20][C:18](=[O:19])[NH:17][C@@H:14]1[CH2:15][CH2:16][C@H:11]([NH2:10])[C@H:12]([CH2:25][CH2:26][CH:27]([CH3:28])[CH3:29])[CH2:13]1)([CH3:24])([CH3:23])[CH3:22]

Participants

4

Reactant 1

HCID 69286608HCID 69286608, compound

Product 1

HCID 69285468HCID 69285468, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A sample of [(1S,2R,4R)-[4-tert-butoxycarbonylamino-2-(3-methyl-but-1-enyl)-cyclohexyl]-carbamic acid benzyl ester (0.24 g, 0.57 mmol) was dissolved in methanol (8 mL) and the resultant solution was charged with 5% Pd/C, Degussa (47 mg). The flask was evacuated and back-filled with hydrogen; this was repeated three times. The reaction was stirred under 1 atm of hydrogen for 14 h before being filtered and concentrated in vacuo to afford (1R,3R,4S)-[4-amino-3-(3-methyl-butyl)-cyclohexyl]-carbamic acid tert-butyl ester. MS found: (M+H)+=285.3.

Workup

  1. customThe flask was evacuated
  2. additionback-filled with hydrogen
  3. filtrationbefore being filtered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9e04835157894df5a92f3093a144d828
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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