m-Nitroacetophenone → (R)-1-(3-nitrophenyl)ethanol

温度

0 °C

To a solution of (1S,2R)-(−)-cis-1-amino-2-indanol (1.49 g, 10 mmol) in tetrahydrofuran (100 mL), cooled to 0° C., was added borane-N,N-diethylaniline complex (17.8 mL, 100 mmol) and the mixture was stirred at 0° C. for 1 hour. After this time a solution of 3′-nitroacetophenone (16.5 g, 100 mL) in tetrahydrofuran (300 mL) was added dropwise over 4 hours and the mixture was allowed to warm to room temperature over night with stirring. After this time the mixture was quenched by stirring with acetone (40 mL) for 1 hour after which it was concentrated under reduced pressure. The yellow residue was dissolved in toluene (250 mL) and washed sequentially with dilute aqueous sulfuric acid (1M, 4×100 mL), water (100 mL), saturated aqueous sodium hydrogen carbonate (100 mL), water (100 mL) and brine (100 mL). The organic solution was dried over MgSO4 and concentrated under reduced pressure to give (1R)-1-(3-nitrophenyl)ethanol (14.3 g, 86%).

1. additionwas added borane-N,N-diethylaniline complex (17.8 mL, 100 mmol)
2. temperatureto warm to room temperature over night
3. stirringwith stirring
4. customAfter this time the mixture was quenched
5. stirringby stirring with acetone (40 mL) for 1 hour after which it
6. concentrationwas concentrated under reduced pressure
7. dissolutionThe yellow residue was dissolved in toluene (250 mL)
8. washwashed sequentially with dilute aqueous sulfuric acid (1M, 4×100 mL), water (100 mL), saturated aqueous sodium hydrogen carbonate (100 mL), water (100 mL) and brine (100 mL)
9. dry with materialThe organic solution was dried over MgSO4
10. concentrationconcentrated under reduced pressure

ORDレコード

ord-ad45301c78884c91acfc7d435b1f93a4

出典データセット

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08461161B2