Acetic Acid → N-BOC-2-cyclohexylethylamine

HRID 361789Notes

Reaction equation

HRID 361789 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 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-f4f26d5199f64b5f81b5bb2af41ca5ec
Source dataset
uspto-grants-1999_02
Patent number
US05866685

Reaction notes

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