Aluminium lithium hydride → 2-(((3aR,4S,6R,6aS)-6-(7-(((1R,2S)-2-(3,4-Difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-1,2,3-triazolo(4,5-d)pyrimidin-3-yl)tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl)oxy)ethanol

Participants

Reaction Conditions

Reaction Steps

LiAlH4 (0.151 g) was added to THF (35 mL) slowly at −10° C. To this mixture was added a solution of compound 11a (1.5 g) in THF (15 mL) slowly over 30 min at 0 to −10° C. The reaction mixture was stirred at 0 to −10° C. for 2 hrs. The reaction was monitored by TLC. When the reaction was complete, it was quenched by addition of aqueous saturated ammonium chloride (10 mL), followed by addition of ethyl acetate (20 mL). The phases were separated and the organic phase was concentrated. The residue was purified by column chromatography (eluting with 40% ethyl acetate in hexane). The fractions containing the product were concentrated under reduced pressure to provide compound 12 as an oily mass (0.7 g, 70-75% yield).

Provenance & Evidence