Toluene → (S)-Ethyl 2-(1-phenylethylamino)cyclohex-1-enecarboxylate

HRID 2065927Notes

Reaction equation

HRID 2065927 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.C1(C)C=CC=CC=1>C(#N)C>[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

5

Reactant 3

HCID 1140TolueneHCID 758181-Phenethylamine, (-)-HCID 95543Ethyl 2-oxocyclohexanecarboxylate

Product 1

HCID 11737390(S)-Ethyl 2-(1-phenylethylamino)cyclohex-1-enecarboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In another embodiment, the present invention may utilize ethyl 2-oxocyclohexane carboxylate (6) to prepare (1S,2S)-2-[(S)-1-phenylethyl amino]cyclohexyl)methanol (11) as described in FIG. 4 by modification of methods of synthesis using an aprotic solvent to produce an amine [See Xu D et al., Tetrahedron Asymmetry, Vol. 8, No. 9, pp/1445-51, 1997]. The current embodiment may comprise reacting ethyl 2-oxocyclohexane carboxylate (6) with (S)-(−)-1-phenylethylamine (7) in the presence of an aprotic solvent including, but not limited to, toluene and acetonitrile, to produce (S)-Ethyl 241-phenylethylamino)cyclohex-1-enecarboxylate (8). The ratio of compound (6) to compound (7) generally ranges from approximately 10:1 to approximately 1:10. In one embodiment, the ratio of compound (6) to compound (7) ranges from approximately 5:1 to approximately 1:5. In another embodiment, the ratio of compound (6) to compound (7) ranges from approximately 2:1 to approximately 1:2. In an additional embodiment, the ratio of compound (6) to compound (7) comprises approximately 1:1.05.

Sources & evidence

ORD record
ord-cb7afc3fc6f54fa0a24a651ef1c3d12b
Source dataset
uspto-grants-2012_10
Patent number
US08288565B2

Reaction notes

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