1-Phenethylamine, (-)- → (S)-Ethyl 2-(1-phenylethylamino)cyclohex-1-enecarboxylate

HRID 2065929Notes

Reaction equation

HRID 2065929 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[C:13]1([C@@H:19]([NH2:21])[CH3:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>[C:13]1([C@@H:19]([NH:21][C:2]2[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=2[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 758181-Phenethylamine, (-)-HCID 95543Ethyl 2-oxocyclohexanecarboxylate

Product 1

HCID 11737390(S)-Ethyl 2-(1-phenylethylamino)cyclohex-1-enecarboxylateYield 111.6%

Reagents, catalysts & solvents 1

HCID 2733225Ytterbium triflateCatalyst

Conditions

Temperature
3 °C

Procedure

Ethyl 2-oxocyclohexane carboxylate (6, 484.9 g) and (S)-(−)-1-phenylethylamine (7, 362.5 g) were charged into an RB flask followed by heptanes (1.5 L) and Ytterbium (III) trifluoromethane sulfonate (8.8 g). The contents were heated to reflux for 3 hours and the liberated water was removed simultaneously and then cooled to 22° C. (±3° C.). The insoluble material was filtered and the filtrate was concentrate on a rotary evaporator under vacuum to afford 869.4 g of (S)-ethyl 2-(1-phenylethylamino)cyclohex-1-enecarboxylate (8) as an oil.

Workup

  1. temperatureThe contents were heated
  2. temperatureto reflux for 3 hours
  3. customthe liberated water was removed simultaneously
  4. filtrationThe insoluble material was filtered
  5. concentrationthe filtrate was concentrate on a rotary evaporator under vacuum

Sources & evidence

ORD record
ord-51615ba6b9f849849e39a4ca0d6c541b
Source dataset
uspto-grants-2012_10
Patent number
US08288565B2

Reaction notes

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