Methyl (1R,3R,4S)-3-azido-4-[(tert-butoxycarbonyl)amino]cyclohexane-1-carboxylate → HCID 68905578, compound

HRID 459518Notes

Reaction equation

HRID 459518 reaction equation
[N:1]([C@H:4]1[C@@H:9]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8][CH2:7][C@@H:6]([C:18]([O:20][CH3:21])=[O:19])[CH2:5]1)=[N+]=[N-].[H][H]>C(OCC)(=O)C.[Pd]>[C:14]([O:13][C:11]([NH:10][C@@H:9]1[CH2:8][CH2:7][C@H:6]([C:18]([O:20][CH3:21])=[O:19])[CH2:5][C@@H:4]1[NH2:1])=[O:12])([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 2

HCID 57416171Methyl (1R,3R,4S)-3-azido-4-[(tert-butoxycarbonyl)amino]cyclohexane-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 68905578HCID 68905578, compoundYield 104.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Methyl (1R*,3R*,4S*)-3-azido-4-(N-tert-butoxycarbonylamino)cyclohexane-1-carboxylate (230 mg) was dissolved in ethyl acetate (8 ml), and a catalytic amount of 10% palladium on carbon was added to stir the mixture at room temperature for 20 hours in a hydrogen atmosphere. Insoluble matter was removed by filtration, and the filtrate was concentrated under reduced pressure to obtain the title compound (220 mg) as a pale yellow oil.

Workup

  1. customInsoluble matter was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-31d0aba74e1747eebbca712da83c77e3
Source dataset
uspto-grants-2007_03
Patent number
US07192968B2

Reaction notes

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