Aluminum(III) Chloride → 2-Phenylethanol

To a cooled (0° C.) mixture of anhydrous AlCl3 (4.70 g, 35 mmol) in THF (120 mL) is slowly added lithium aluminum hydride (4.34 g, 115 mmol), and the resulting mixture is stirred at the same temperature for 30 min. To the resulting stirred and cooled (−78° C.) THF mixture is added a solution of trans-(3S,7aS)-7a-[4-(benzyloxymethyl)cyclohexyl]-3-phenyltetrahydropyrrolo[2,1-b]oxazol-5-one (15.5 g, 38 mmol) in THF (80 mL) over 30 min. The resulting mixture is stirred at the same temperature for 1.5 hours, and then warmed to room temperature and stirred for additional 15 min. The resulting mixture is cooled to 0° C., quenched with the careful addition of Na2SO4-10H2O (5.0 g), and stirred for additional 30 min at room temperature. The insoluble matter is filtered and the filtrate is concentrated in vacuo to afford crude trans-(S)-2-{(R)-2-[4-benzyloxymethyl)cyclohexyl]pyrrolidin-1-yl}-2-phenylethanol, which is used without further purification.

1. temperatureTo a cooled
2. stirringTo the resulting stirred
3. stirringThe resulting mixture is stirred at the same temperature for 1.5 hours
4. stirringstirred for additional 15 min
5. temperatureThe resulting mixture is cooled to 0° C.
6. customquenched with the careful addition of Na2SO4-10H2O (5.0 g)
7. stirringstirred for additional 30 min at room temperature
8. filtrationThe insoluble matter is filtered
9. concentrationthe filtrate is concentrated in vacuo

ORD record

ord-98879f5e19204c9db77d275919427178

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08410275B2