HCID 11550473, compound → (1R,2S)-N1-(tert-Butoxycarbonyl)-1,2-cyclohexanediamine

HRID 2421063Notes

Reaction equation

HRID 2421063 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@@H:9]1[N:14]=[N+]=[N-])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:17])[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@@H:9]1[NH2:14])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 11550473HCID 11550473, compound

Product 1

HCID 1514392(1R,2S)-N1-(tert-Butoxycarbonyl)-1,2-cyclohexanediamineYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of compound (1R,2S) (2-Azidocyclohexyl-carbamic acid) tert-butyl ester (1.8 g, 7.5 mmol) in methanol (20 mL), 10% Pd—C (360 mg) was added and hydrogenated at 32 psi for 4 h Parr hydrogenator. The reaction mixture was filtered on a celite pad and the filterate was concentrated to give the title compound as a solid (1.1 g, 69%), which was used without further purification. MS: (M+1): 215.07

Workup

  1. filtrationThe reaction mixture was filtered on a celite pad
  2. concentrationthe filterate was concentrated

Sources & evidence

ORD record
ord-45adb2bb2a3443f797f50c7ea69f415d
Source dataset
uspto-grants-2011_06
Patent number
US07956069B2

Reaction notes

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