Methanol → HCID 18517940, compound

HRID 1369055Notes

Reaction equation

HRID 1369055 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:15]O>>[CH3:15][NH:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 30183432-Benzylcyclohexan-1-amine

Product 1

HCID 18517940HCID 18517940, compoundYield 14%

Procedure

To a solution of 1-amino-2-benzylcyclohexane (an intermediate in preparation I, 0.90 gm, 4.8 mmol) and methanol (25 mL) was added RhH(Ph3P)3 (275 mg, 0.24 mmol) and the reaction mixture heated to reflux for 12 h. After cooling to room temperature, the solvent was removed under vacuum and the residue chromatographed on neutral alumina with ether and then on silica gel with triethylamine/ethyl acetate/hexane to give the title compound isolated as an oil in 14% yield.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux for 12 h
  3. customthe solvent was removed under vacuum
  4. customthe residue chromatographed on neutral alumina with ether

Sources & evidence

ORD record
ord-712b825d16284407ad274dcf88ac71a4
Source dataset
uspto-grants-2003_06
Patent number
US06576632B1

Reaction notes

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