Borane → (1S)-3-amino-1-phenylpropan-1-ol

To 10 ml of a THF solution of 1.47 g (10.0 mmol) of the (S)-3-hydroxy-3-phenylpropanenitrile obtained in Example 1, slowly added was 1.23 ml (13.0 mmol) of borane.dimethylsulfide complex. After removing the dimethylsulfide by reducing the pressure, the reaction mixture was refluxed for 2.5 hours. The reaction was stopped by the addition of a methanol/hydrochloric acid solution, and the methanol was distilled off under vacuum. After neutralizing with a 5N aqueous solution of sodium hydroxide, the solvent was distilled off, a further aqueous solution of sodium hydroxide was added to make the reaction solution basic, and this was then extracted with methylene chloride. This methylene chloride solution was dried with anhydrous sodium sulfate, and the solvent was then distilled off under vacuum to give 1.47 g of (S)-3-amino-1-phenylpropanol. The amino group of (S)-3-amino-1-phenylpropanol was monobenzoylated by reaction with benzoyl chloride, and when it was analyzed using a CHIRALCEL OB column (manufactured by Daicel Chemical Industries, Ltd., eluant; n-hexane:2-propanol=90:10) it was found that the optical purity was 98% ee.

1. customAfter removing the dimethylsulfide
2. temperaturethe reaction mixture was refluxed for 2.5 hours
3. additionThe reaction was stopped by the addition of a methanol/hydrochloric acid solution
4. distillationthe methanol was distilled off under vacuum
5. distillationthe solvent was distilled off
6. additiona further aqueous solution of sodium hydroxide was added
7. extractionthis was then extracted with methylene chloride
8. dry with materialThis methylene chloride solution was dried with anhydrous sodium sulfate
9. distillationthe solvent was then distilled off under vacuum

ORDレコード

ord-1aca8464d4ae4a66ac4370a57af6b83d

出典データセット

uspto-grants-2004_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06686505B2