Water → Tert-butyl (2S)-2-[(3-fluoro-4-methylphenyl)(hydroxy)methyl]pyrrolidine-1-carboxylate
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[CH3:22])[C:5]([C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:6].[BH4-].[Na+].O>CO>[F:1][C:2]1[CH:3]=[C:4]([CH:5]([OH:6])[C@@H:7]2[CH2:11][CH2:10][CH2:9][N:8]2[C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])[CH:19]=[CH:20][C:21]=1[CH3:22]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of tert-butyl (2S)-2-(3-fluoro-4-methylbenzoyl)pyrrolidine-1-carboxylate (1.35 g, 4.38 mmol), which had been obtained in Example 1 (1a), in methanol (5 mL), sodium borohydride (0.20 g, 5.23 mmol) was added under ice cooling, and stirred at room temperature for 0.5 hours. Water (20 mL) was added to the reaction solution, which was then extracted with ethyl acetate (20 mL×3). After that, the organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (n-hexane/ethyl acetate=3/1) to give the title compound as an orange oily substance (1.30 g, yield 96%).
Workup
- extractionwas then extracted with ethyl acetate (20 mL×3)
- washwashed with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- distillationThe solvent was distilled off under reduced pressure
- customThe residue was purified by silica gel chromatography (n-hexane/ethyl acetate=3/1)
Sources & evidence
- ORD record
- ord-8828d568a4d0493d8ed254fbd5d9bbc7
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08173631B2
Reaction notes
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