Lithium aluminum hydride → N-[((1S,2S,4R)-2-[tert-butyl(dimethyl)silyl]oxy-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentyl)methyl]-N-methylsulfamide

Participants

Reaction Conditions

Reaction Steps

tert-Butyl(aminosulfonyl)[((1S,2S,4R)-2-[tert-butyl(dimethyl)silyl]oxy-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentyl)-methyl]carbamate (108 mg, 0.000164 mol) was dissolved in tetrahydrofuran (2.0 mL) under an atmosphere of nitrogen. Lithium tetrahydroaluminate (12.5 mg, 0.000329 mol) was added and the mixture heated at 50° C. for 80 minutes. The reaction was then cooled, quenched with water and acidified to ˜pH 6 with 1M HCl. This mixture was then extracted with ethyl acetate, the separated organic phase was evaporated, and the residue was purified by silica gel chromatography, eluting with 10 to 100% ethyl acetate in hexanes, to yield the product, 25 mg (27%). LC/MS: Rt=2.34 min, ES+ 571 (AA standard).

Provenance & Evidence