Sodium borohydride → [(3S,4S,5R,6S)-3,4,5-tri-benzyloxy-6-[4-chloro-3-[(2,3-difluoro-4-methoxy-phenyl)methyl]phenyl]-2-(hydroxymethyl)-6-methoxy-tetrahydropyran-2-yl]methanol

To a solution of (2R,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[(2,3-difluoro-4-methoxy-phenyl)methyl]phenyl]-2-(hydroxymethyl)-6-methoxy-tetrahydropyran-2-carbaldehyde 21m (0.52 g, 0.68 mmol) in methanol (20 mL) was added sodium borohydride (52 mg, 1.37 mmol) at 0° C. The mixture was warmed up to room temperature and stirred for 4 hours. The reaction mixture was quenched with saturated aqueous ammonium chloride (15 mL) and 20 mL of water was added. The mixture was extracted with ethyl acetate (20 mL×4). The combined organic layers were dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound 21n as light yellow oil (0.52 g, 100%). This material was not further purified

1. customThe reaction mixture was quenched with saturated aqueous ammonium chloride (15 mL) and 20 mL of water
2. additionwas added
3. extractionThe mixture was extracted with ethyl acetate (20 mL×4)
4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
5. filtrationfiltered
6. concentrationThe filtrate was concentrated in vacuo

ORD-Eintrag

ord-d14be5a92737469a862ddb685fba50fa

Quelldatensatz

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09394329B2