Methyl 2-(3-cyclohexyl-1,1,1-trifluoro-3-nitropropan-2-ylamino)-3,3-dimethylbutanoate → Methyl 2-(3-amino-3-cyclohexyl-1,1,1-trifluoropropan-2-ylamino)-3,3-dimethylbutanoate

HRID 424969Notes

Reaction equation

HRID 424969 reaction equation
[CH:1]1([CH:7]([N+:23]([O-])=O)[CH:8]([NH:13][CH:14]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:15]([O:17][CH3:18])=[O:16])[C:9]([F:12])([F:11])[F:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)C.[Ni]>[NH2:23][CH:7]([CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[CH:8]([NH:13][CH:14]([C:19]([CH3:22])([CH3:20])[CH3:21])[C:15]([O:17][CH3:18])=[O:16])[C:9]([F:12])([F:10])[F:11]

Participants

4

Reactant 1

HCID 66704841Methyl 2-(3-cyclohexyl-1,1,1-trifluoro-3-nitropropan-2-ylamino)-3,3-dimethylbutanoate

Product 1

HCID 66704763Methyl 2-(3-amino-3-cyclohexyl-1,1,1-trifluoropropan-2-ylamino)-3,3-dimethylbutanoate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Methyl 2-(3-cyclohexyl-1,1,1-trifluoro-3-nitropropan-2-ylamino)-3,3-dimethylbutanoate (isomer 5B1, 0.3 gm) in ethanol (30 mL) was hydrogenated over Raney Ni catalyst at 50 psi for 20 hours. The catalyst was filtered off and the filtrate was evaporated to dryness under reduced pressure, to provide crude methyl 2-(3-amino-3-cyclohexyl-1,1,1-trifluoropropan-2-ylamino)-3,3-dimethylbutanoate (6) which was used in the next reaction with no further purification.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-c3596a17ae024defaaac21b6767f9c1d
Source dataset
uspto-grants-2012_01
Patent number
US08106059B2

Reaction notes

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