1-Phenethylamine, (-)- → (1R,2S)-N-[(1R)-1-phenylethyl]-2-(trifluoromethyl)cyclohexanamine

HRID 1696220Notes

Reaction equation

HRID 1696220 reaction equation
[F:1][C:2]([F:11])([F:10])[CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=O.[C:12]1([C@@H:18]([NH2:20])[CH3:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(=O)([O-])O.[Na+]>ClCCCl>[C:12]1([C@H:18]([NH:20][C@@H:4]2[CH2:5][CH2:6][CH2:7][CH2:8][C@@H:3]2[C:2]([F:11])([F:10])[F:1])[CH3:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 758181-Phenethylamine, (-)-HCID 516892Sodium BicarbonateHCID 27774882-(Trifluoromethyl)cyclohexanoneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 67278095(1R,2S)-N-[(1R)-1-phenylethyl]-2-(trifluoromethyl)cyclohexanamineYield 48%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a 1,2-dichloroethane solution of 2-(trifluoromethyl)cyclohexanone (10.0 g) and [(1S)-1-phenylethyl]amine (7.29 g) was added NaBH(OAc)3(25.51 g) at ambient temperature. After stirring for 2 days at ambient temperature, 150 mL of saturated aqueous sodium hydrogencarbonate was added. After extraction with EtOAc, combined organic layer was dried over MgSO4, filtered and evaporated to dryness in vacuo. The crude residue was purified by silica gel column chromatography (n-hexane:EtOAc=8:1 to 2:1) to give (1R,2S)—N-[(1R)-1-phenylethyl]-2-(trifluoromethyl)cyclohexanamine (7.83 g) as a white solid.

Workup

  1. extractionAfter extraction with EtOAc
  2. dry with materialwas dried over MgSO4
  3. filtrationfiltered
  4. customevaporated to dryness in vacuo
  5. customThe crude residue was purified by silica gel column chromatography (n-hexane:EtOAc=8:1 to 2:1)

Sources & evidence

ORD record
ord-a9974bbad6cb48048f0fcfe2596f164d
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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