Water → ((3R,4S)-1-Benzyl-4-phenylpyrrolidin-3-YL)methanol

To (S)-3-((3R,4S)-1-benzyl-4-phenyl-pyrrolidine-3-carbonyl)-4-phenyl-oxazolidin-2-one (9.96 g, 23.35 mmol) in THF (100 mL) in a three-necked flask equipped with a thermometer and addition funnel was added lithium aluminium hydride (48 mL, 1M in THF) dropwise so that the temperature did not exceed 40° C. while keeping the reaction vessel in a water bath. When addition was complete the water bath was removed and the reaction stirred at room temperature overnight. The reaction was carefully quenched with water (1.6 mL), NaOH (1.6 mL, 2N) and water (4.5 mL). After stirring for 15 minutes, the reaction mixture was filtered through a pad of celite and rinsed with THF (40 mL). The filtrate was concentrated to give a pale yellow oil, which was purified by flash silica gel chromatography eluting with ethyl acetate:hexanes (1:1) to give 3.38 g (55%) of ((3R,4S)-1-benzyl-4-phenyl-pyrrolidin-3-yl)-methanol.

1. customdid not exceed 40° C.
2. additionWhen addition
3. customwas removed
4. customThe reaction was carefully quenched with water (1.6 mL), NaOH (1.6 mL, 2N) and water (4.5 mL)
5. stirringAfter stirring for 15 minutes
6. filtrationthe reaction mixture was filtered through a pad of celite
7. washrinsed with THF (40 mL)
8. concentrationThe filtrate was concentrated
9. customto give a pale yellow oil, which
10. customwas purified by flash silica gel chromatography
11. washeluting with ethyl acetate:hexanes (1:1)

ORD record

ord-299cec936e7a4442bd43484ed4c37e26

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08076349B2