反应详情

温度

25 °C

To a solution of methyl 4-allyl-3-(4-benzyloxyazepan-1-yl)sulfonyl-benzoate (630.00 mg, 1.42 mmol, 1.00 Eq) in THF (10 mL) and H2O (2 mL) were added OsO4 (36.10 mg, 142.00 umol, 0.10 Eq) and NaIO4 (607.45 mg, 2.84 mmol, 2.00 Eq) at 0° C. The mixture was stirred at 25° C. for 3 hr. TLC detected the reaction was complete, the mixture was poured into saturated Na2S2O3 solution, extracted with DCM, the combined organic layer was dried over anhydrous Na2SO4, concentrated, the residue was diluted in MeOH (10 mL), to the formed mixture was added NaBH3CN (88.86 mg, 1.41 mmol, 1.00 Eq). The mixture was stirred at 25° C. for 3 hr. TLC detected the reaction was complete, the reaction was quenched with water, extracted with EA, the combined organic layer was dried over anhydrous Na2SO4, concentrated, the residue was purified by chromatography (silica gel, eluting with PE:EA=3:1 to 1:1) to afford product methyl 3-(4-benzyloxyazepan-1-yl)sulfonyl-4-(2-hydroxyethyl)benzoate (340.00 mg, 759.71 umol, 53.88% yield). LCMS: 448 [M+1].

1. extractionextracted with DCM
2. dry with materialthe combined organic layer was dried over anhydrous Na2SO4
3. concentrationconcentrated
4. additionthe residue was diluted in MeOH (10 mL), to the formed mixture
5. stirringThe mixture was stirred at 25° C. for 3 hr
6. customthe reaction was quenched with water
7. extractionextracted with EA
8. dry with materialthe combined organic layer was dried over anhydrous Na2SO4
9. concentrationconcentrated
10. customthe residue was purified by chromatography (silica gel, eluting with PE:EA=3:1 to 1:1)