tert-Butyl [(1S,2R)-2-azidocyclohexyl]carbamate → (1S,2R)-Cyclohexane-1,2-diamine, N1-BOC protected

HRID 459471

Reaction equation

HRID 459471 reaction equation
[N:1]([C@@H:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C@@H:5]1[NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[N+]=[N-]>CO.[Pd]>[C:14]([O:13][C:11]([NH:10][C@H:5]1[CH2:6][CH2:7][CH2:8][CH2:9][C@H:4]1[NH2:1])=[O:12])([CH3:17])([CH3:15])[CH3:16]

Participants

4

Reactant 1

HCID 57416183tert-Butyl [(1S,2R)-2-azidocyclohexyl]carbamate

Product 1

HCID 1514389(1S,2R)-Cyclohexane-1,2-diamine, N1-BOC protectedYield 93.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(1R,2S)-1-Azido-2-(tert-butoxycarbonylamino)-cyclohexane (174 mg) was dissolved in methanol (10 ml), and to the solution 10% palladium on carbon (120 mg) was added to conduct catalytic reduction under atmospheric pressure. The catalyst was separated by filtration, and the filtrate was concentrated to obtain a crude title compound (145 mg) as a colorless amorphous substance. This compound was used in the next reaction without purifying it.

Workup

  1. customThe catalyst was separated by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ae2f5fdfeeac422ab47666376c9e13f7
Source dataset
uspto-grants-2007_03
Patent number
US07192968B2

Linked notes

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