HCID 69285761, compound → HCID 131726908, compound

HRID 2225283Notes

Reaction equation

HRID 2225283 reaction equation
[C:1]([O:5][C:6](=[O:30])[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][S:26]([CH3:29])(=[O:28])=[O:27])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[NH2:14][C@H:11]1[CH2:12][CH2:13][C@@H:8]([NH:7][C:6](=[O:30])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:9][C@H:10]1[CH2:25][S:26]([CH3:29])(=[O:28])=[O:27]

Participants

5

Reactant 2

HCID 69285761HCID 69285761, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131726908HCID 131726908, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(1R,3R,4S)-(4-Benzyloxycarbonylamino-3-(methyl)sulfonylmethylcyclohexyl)carbamic acid tert-butyl ester (300 mg) was dissolved in MeOH (5 ml) prior to the addition of 10% Pd/C (200 mg). A hydrogen balloon was added and the solution was stirred for 3 h. The palladium was filtered off and the solution was concentrated to give tert-butyl(1R,3R,4S)-4-amino-3-(methylsulfonylmethyl)cyclohexylcarbamate (201 mg). MS found: (M+H)+307.2.

Workup

  1. filtrationThe palladium was filtered off
  2. concentrationthe solution was concentrated

Sources & evidence

ORD record
ord-093c94af2c324be4b72c1bc6061efe36
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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