Triethylamine → Tert-butyl 4-(2-oxo-2-(3-(trifluoromethoxy)phenyl)ethylcarbamoyl)piperidine-1-carboxylate
Reaction equation
C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC.[NH2:20][CH2:21][C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:31]([F:34])([F:33])[F:32])[CH:25]=1)=[O:23].[C:35]([O:39][C:40]([N:42]1[CH2:47][CH2:46][CH:45]([C:48](O)=[O:49])[CH2:44][CH2:43]1)=[O:41])([CH3:38])([CH3:37])[CH3:36]>C(Cl)Cl>[O:23]=[C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:31]([F:32])([F:33])[F:34])[CH:25]=1)[CH2:21][NH:20][C:48]([CH:45]1[CH2:46][CH2:47][N:42]([C:40]([O:39][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:41])[CH2:43][CH2:44]1)=[O:49]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Add triethylamine (1.1 mL, 7.89 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (1.51 g, 7.87 mmol) to a solution of 2-amino-1-(3-(trifluoromethoxy)phenyl)ethanone (1.56 g, 6.10 mmol) and 1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (1.66 g, 7.24 mmol) in CH2Cl2 (15 mL) at 0° C. Stir at 0° C. for 3 h, then at room temperature overnight. Concentrate the mixture in vacuo. Purify the residue by silica gel chromatography (80 g SiO2 eluting with 50% ethyl acetate/hexanes, 1 L) to provide tert-butyl 4-(2-oxo-2-(3-(trifluoromethoxy)phenyl)ethylcarbamoyl)piperidine-1-carboxylate (1.50 g, 57%).
Workup
- customat room temperature
- customovernight
- concentrationConcentrate the mixture in vacuo
- customPurify the residue by silica gel chromatography (80 g SiO2 eluting with 50% ethyl acetate/hexanes, 1 L)
Sources & evidence
- ORD record
- ord-a266332069cf451394046cbd4b072f52
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08093383B2
Reaction notes
Loading…