Dimethylformamide → (S)-tert-butyl 1-(3-fluoro-4-formylphenyl)ethylcarbamate
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[CH:4][C:3]=1[F:18].[Li]CCCC.CN([CH:27]=[O:28])C.CCOC(C)=O.CCCCCCC>C1COCC1>[F:18][C:3]1[CH:4]=[C:5]([C@@H:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])[CH:6]=[CH:7][C:2]=1[CH:27]=[O:28]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
A solution of (S)-tert-butyl 1-(4-bromo-3-fluorophenyl)ethylcarbamate (318 mg, 1 mmol) in dry THF (5 mL) was cooled to −78° C. BuLi (2.5 M, 840 μL, 2.1 mmol) was added dropwise and the resulting solution was stirred at −78° C. for 1 h. Then DMF (232 μL, 3.00 mmol) was added in one portion. The reaction was stirred for another 30 min at −78° C. then quenched with sat. NH4Cl solution. The reaction was stirred at room temperature for another 30 min then diluted with EtOAc, washed with water and brine. The separated organic was dried over Na2SO4, filtered and concentrated. Silica gel column chromatography (EtOAc/heptane 0 to 80%) provided (S)-tert-butyl 1-(3-fluoro-4-formylphenyl)ethylcarbamate as a white solid (70 mg, 26.2% yield).
Workup
- stirringThe reaction was stirred for another 30 min at −78° C.
- customthen quenched with sat. NH4Cl solution
- stirringThe reaction was stirred at room temperature for another 30 min
- additionthen diluted with EtOAc
- washwashed with water and brine
- dry with materialThe separated organic was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-7bc15e9c4bc544cd8e1e54dbea52e2e3
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08957068B2
Reaction notes
Loading…