Acetic Acid → N-BOC-2-cyclohexylethylamine

HRID 1007751Notes

Reaction equation

HRID 1007751 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(O)(=O)C>CO.[Rh]>[C:1]([NH:8][CH2:9][CH2:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 3541750tert-butyl N-(2-phenylethyl)carbamate

Product 1

HCID 19878080N-BOC-2-cyclohexylethylamine

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

Procedure

N-BOC-2-phenylethylamine (3.1 g) and 5% rhodium on alumina (1.1 g) are combined in methanol (40 ml) containing acetic acid (1.0 ml). The mixture is shaken under hydrogen at 50 psi for about 20 hours. The mixture is filtered, evaporated in vacuo, and the residue taken up into ethyl acetate. The organic solution is washed with water, 5% sodium bicarbonate solution, water, brine, dried over sodium sulfate, filtered, and evaporated in vacuo to to give N-BOC-2-cyclohexylethylamine.

Workup

  1. filtrationThe mixture is filtered
  2. customevaporated in vacuo
  3. washThe organic solution is washed with water, 5% sodium bicarbonate solution, water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-335b938de8c24b6eb7e77d0091b604bd
Source dataset
uspto-grants-2004_09
Patent number
US06797700B2

Reaction notes

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