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0 °C

To an ice-cooled solution of 2-{4-[8-fluoro-2-(2-isopropyl-5-methyl-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 (0.394 mmol) in THF (20 mL) was added LiAlH4 (1.0M in THF, 0.79 mL) and the mixture was stirred at 0° C. for 5 min. To the reaction mixture was added EtOAc (1 mL) and stirring was continued for 10 min. Volatiles were removed under reduced pressure and the resulting residue was partitioned between DCM (40 mL) and 10% aq. solution of Rochelle's salt (50 mL). The suspension was then filtered through a pad of Celite®. The filtrate was extracted with additional DCM and the combined organic layers were washed with water, then brine, dried and concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, gradient 2-10% 2M NH3/MeOH in DCM) affording 2-{4-[8-Fluoro-2-(2-isopropyl-5-methyl-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 (148 mg, 73% over two steps). LCMS: RT 2.17 min [M+H]+ 515.0

1. stirringstirring
2. waitwas continued for 10 min
3. customVolatiles were removed under reduced pressure
4. customthe resulting residue was partitioned between DCM (40 mL) and 10% aq. solution of Rochelle's salt (50 mL)
5. filtrationThe suspension was then filtered through a pad of Celite®
6. extractionThe filtrate was extracted with additional DCM
7. washthe combined organic layers were washed with water
8. dry with materialbrine, dried
9. concentrationconcentrated in vacuo
10. customThe resulting residue was purified by column chromatography (Si-PCC, gradient 2-10% 2M NH3/MeOH in DCM)