反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
AUXILIARIES
试剂、催化剂与溶剂
CONDITIONS
反应条件
- 温度
- 0 °C
PROCEDURE
实验过程
To an ice-cooled solution of 2-methyl-2-[4-(2-pyridin-2-yl-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-9-ylsulfanyl)piperidin-1-yl]propionic acid methyl ester (0.438 mmol) in THF (20 mL) was added LiAlH4 (1.0M in THF, 1.32 mL) and the mixture was stirred at 0° C. for 30 min. To the reaction mixture was added EtOAc (0.5 mL) and stirring was continued for 10 min. Volatiles were removed under reduced pressure and the resulting residue was partitioned between DCM and 10% aq. solution of Rochelle's salt. The suspension was then filtered through a pad of Celite®. The filtrate was extracted with additional DCM and the combined organic phases were washed with water, then brine, 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-Methyl-2-[4-(2-pyridin-2-yl-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-9-ylsulfanyl)piperidin-1-yl]propan-1-ol as a colorless gum (190 mg, 96% over two steps). LCMS: RT 1.799 min [M+H]+ 451.1
WORKUP
后处理
- stirringstirring
- waitwas continued for 10 min
- customVolatiles were removed under reduced pressure
- customthe resulting residue was partitioned between DCM and 10% aq. solution of Rochelle's salt
- filtrationThe suspension was then filtered through a pad of Celite®
- extractionThe filtrate was extracted with additional DCM
- washthe combined organic phases were washed with water
- dry with materialbrine, dried
- concentrationconcentrated in vacuo
- customThe resulting residue was purified by column chromatography (Si-PCC, gradient 2-13% 2M NH3/MeOH in DCM)