反应详情

Add lithium borohydride (1.03 g, 47.4 mmol) to an ice cold solution of 4-(R)-fluoropyrrolidine-N1,2-(R)-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (7.8 g, 31.5 mmol) in THF (100 mL). Let warm to room temperature over 18 h. Cool in ice bath. Slowly add acetic acid (5 mL) and water and extract with ethyl acetate. Wash extract with water, saturated aqueous sodium bicarbonate solution, saturated aqueous sodium chloride, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with hexanes and ethyl acetate) to give the title compound as a thick oil (5.56 g, 80%).

1. temperatureCool in ice bath
2. extractionSlowly add acetic acid (5 mL) and water and extract with ethyl acetate
3. washWash
4. extractionextract with water, saturated aqueous sodium bicarbonate solution, saturated aqueous sodium chloride
5. dry with materialdry (magnesium sulfate)
6. concentrationconcentrate
7. custompurify
8. wash(silica gel chromatography, eluting with hexanes and ethyl acetate)