(+/-)-cis-N1-Benzyl-N2-tert-butoxycarbonyl-N1-methyl-1,2-cyclohexanediamine → (+/-)-cis-N1-tert-Butoxycarbonyl-N2-methyl-1,2-cyclohexane-diamine

HRID 546422Notes

Reaction equation

HRID 546422 reaction equation
[CH2:1]([N:8](C)[C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]1[NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])C1C=CC=CC=1.[H][H]>[Pd].CO>[C:19]([O:18][C:16]([NH:15][C@@H:10]1[CH2:11][CH2:12][CH2:13][CH2:14][C@@H:9]1[NH:8][CH3:1])=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 2

HCID 58822120(+/-)-cis-N1-Benzyl-N2-tert-butoxycarbonyl-N1-methyl-1,2-cyclohexanediamineHCID 178418361HCID 178418361, compound

Product 1

HCID 68907343(+/-)-cis-N1-tert-Butoxycarbonyl-N2-methyl-1,2-cyclohexane-diamineYield 92.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(±)-cis-N1-Benzyl-N2-tert-butoxycarbonyl-N1-methyl-1,2-cyclohexanediamine (1.92 g) was added to methanol (50 ml), 10% palladium on carbon (containing 50% of water, 900 mg) was added, and the mixture was stirred for 20 hours in a hydrogen atmosphere. After separating the catalyst by filtration, the filtrate was concentrated to obtain the title compound (1.27 g) as a colorless oil.

Workup

  1. additionwas added
  2. customAfter separating the catalyst
  3. filtrationby filtration
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-04ce2d99beda4ff4bbf45b46c49b35b7
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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