Aluminium lithium hydride → ((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. When addition was complete, the reaction was 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. customThe reaction was carefully quenched with water (1.6 mL), NaOH (1.6 mL, 2N) and water (4.5 mL)
4. stirringAfter stirring for 15 minutes
5. filtrationthe reaction mixture was filtered through a pad of celite
6. washrinsed with THF (40 mL)
7. concentrationThe filtrate was concentrated
8. customto give a pale yellow oil, which
9. customwas purified by flash silica gel chromatography
10. washeluting with ethyl acetate:hexanes (1:1)

ORD-Eintrag

ord-e7cf686578eb42f296dcec87817891bb

Quelldatensatz

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07288548B2