Ethyl Acetate → 2-{4-[2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-9-ylsulfanyl]piperidin-1-yl}-2-methylpropan-1-ol

Participants

Reaction Conditions

Reaction Steps

To an ice-cooled solution of 2-{4-[2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-9-ylsulfanyl]piperidin-1-yl}-2-methylpropionic acid methyl ester (0.485 mmol) in THF (20 mL) was added LiAlH4 (1.0M in THF, 1.5 mL) and the mixture was stirred at 0° C. for 1 h. To the reaction mixture was added EtOAc (0.5 mL) and stirring was continued for 10 min. Volatiles were then removed under reduced pressure and the resulting residue was partitioned between DCM and 10% aq. solution of Rochelle's salt. The suspension was stirred for 20 min and then filtered through a pad of Celite®. The filtrate was extracted with DCM and the combined organic phases were washed with water, followed by brine, then dried and concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, gradient 2-13% 2M NH3/MeOH in DCM) affording 2-{4-[2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-9-ylsulfanyl]piperidin-1-yl}-2-methylpropan-1-ol (229 mg, 98% over two steps). LCMS: RT 2.13/2.19 min [M+H]+ 483.2

Provenance & Evidence