Aluminium lithium hydride → (S)-tert-butyl 1-(3-fluoro-4-formylphenyl)ethylcarbamate
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@@H:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH3:15])[CH:5]=[CH:6][C:7]=1[C:8](=[O:13])N(OC)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].CCOC(C)=O.CCCCCCC>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C@@H:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH3:15])[CH:5]=[CH:6][C:7]=1[CH:8]=[O:13]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a cooled (0° C.) solution of (S)-tert-butyl 1-(3-fluoro-4-(methoxy(methyl)carbamoyl)phenyl)ethylcarbamate (1.175 g, 3.6 mmol) in THF (36 mL) was added a solution of LAH in THF (1.0 M, 18 mL, 18 mmol) and the resulting mixture was stirred at 0° C. for 20 min. The reaction mixture was quenched by addition of a saturated Na2SO4 solution until gas evolution ceased. The reaction mixture was extracted with EtOAc (2×100 mL). Combined organics were dried over Na2SO4, filtered and concentrated. Silica gel column chromatography (EtOAc/heptane 12 to 100%) provided (S)-tert-butyl 1-(3-fluoro-4-formylphenyl)ethylcarbamate as a white solid (760 mg, 79% yield).
Workup
- customThe reaction mixture was quenched by addition of a saturated Na2SO4 solution until gas evolution
- extractionThe reaction mixture was extracted with EtOAc (2×100 mL)
- dry with materialCombined organics were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-7b66b6e4e00c4b80b11450318218ca4a
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434719B2
Reaction notes
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