4-[(2-Methoxy-ethyl)-(2,2,2-trifluoro-acetyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester → 4-[(2-Methoxy-ethyl)-(2,2,2-trifluoro-ethyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:21][CH2:22][O:23][CH3:24])[C:15](=O)[C:16]([F:19])([F:18])[F:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]([CH2:21][CH2:22][O:23][CH3:24])[CH2:15][C:16]([F:17])([F:18])[F:19])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 4-[(2-methoxy-ethyl)-(2,2,2-trifluoro-acetyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester (685 mg) in dry THF (7 mL) was added borane-methyl sulfide complex (405 uL) at 0° C. under inert atmosphere. The reaction mixture was refluxed for 3 h, and then stirred at room temperature overnight, quenched with MeOH, diluted with DCM, washed with brine, dried (MgSO4) and the solvent removed in vacuo. The residue was purified using flash chromatography to yield 4-[(2-methoxy-ethyl)-(2,2,2-trifluoro-ethyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester as an oil (635 mg). Treatment of this compound with HCl in DCM/MeOH furnished the desired amine, isolated as the hydrochloride salt.
Workup
- temperatureThe reaction mixture was refluxed for 3 h
- customquenched with MeOH
- additiondiluted with DCM
- washwashed with brine
- dry with materialdried (MgSO4)
- customthe solvent removed in vacuo
- customThe residue was purified
Sources & evidence
- ORD record
- ord-9c0948a5688448bd8d1a268828a79cb1
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08153629B2
Reaction notes
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