Tert-butyl 5-oxo-5-(3,4,5-trifluorophenyl)pentylcarbamate → 5-Amino-1-(3,4,5-trifluorophenyl)pentan-1-one

HRID 473794Notes

Reaction equation

HRID 473794 reaction equation
[O:1]=[C:2]([C:15]1[CH:20]=[C:19]([F:21])[C:18]([F:22])=[C:17]([F:23])[CH:16]=1)[CH2:3][CH2:4][CH2:5][CH2:6][NH:7]C(=O)OC(C)(C)C>FC(F)(F)C(O)=O.ClCCl>[NH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]([C:15]1[CH:16]=[C:17]([F:23])[C:18]([F:22])=[C:19]([F:21])[CH:20]=1)=[O:1]

Participants

3

Reactant 1

HCID 67505669Tert-butyl 5-oxo-5-(3,4,5-trifluorophenyl)pentylcarbamate

Product 1

HCID 675060535-Amino-1-(3,4,5-trifluorophenyl)pentan-1-oneYield 88.1%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

Tert-butyl 5-oxo-5-(3,4,5-trifluorophenyl)pentylcarbamate (0.18 g, 0.54 mmol) was stirred in trifluoroacetic acid/dichloromethane 1:1 (8 mL) for 1 hour then concentrated. The residue was dissolved in ethyl acetate (40 mL) and washed with saturated sodium chloride/2M aqueous sodium hydroxide 10:1 (11 mL), then dried over anhydrous sodium sulfate, filtered and concentrated to provide 5-amino-1-(3,4,5-trifluorophenyl)pentan-1-one (0.11 g, 88% yield) as an oil. MS (EI) for C11H12F3NO: 232 (MH+).

Workup

  1. concentrationthen concentrated
  2. dissolutionThe residue was dissolved in ethyl acetate (40 mL)
  3. washwashed with saturated sodium chloride/2M aqueous sodium hydroxide 10:1 (11 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-413055a8a8184245bbc7c9a6a4c17fd8
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

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