Ozone → HCID 58055033, compound

Temperature

23 °C

A solution of tert-butyl (3R,4S)-4-(tert-butyldimethylsilyl)oxy-3-methoxy-3-(prop-2-en-1-yl)pyrrolidine-1-carboxylate (230 mg) in CH2Cl2 (10 mL) was cooled to −78° C. and treated with a stream of ozone until a blue color persisted. A stream of nitrogen was passed through the solution for 15 minutes to remove excess ozone from solution. The solution was then treated with dimethylsulfide (0.2 mL) and allowed to warm to 23° C. over 30 min. Volatile components of the reaction mixture were removed in vacuo. The residue was dissolved in methanol (10 mL). To the solution was added NaBH4 (50 mg) at 0° C. and the mixture was stirred at 0° C. for 30 minutes. The mixture was poured into saturated aqueous solution of NH4Cl and extracted with CHCl3. The extract was washed with brine, dried over MgSO4 and concentrated. The residue was purified with silica gel column chromatography (eluent: hexane/EtOAc=99/1˜1/99) to give tert-butyl (3R,4S)-4-(tert-butyldimethylsilyl)oxy-3-(2-hydroxyethyl)-3-methoxypyrrolidine-1-carboxylate as a pale yellow foam.

1. customto remove excess ozone from solution
2. additionThe solution was then treated with dimethylsulfide (0.2 mL)
3. customVolatile components of the reaction mixture were removed in vacuo
4. dissolutionThe residue was dissolved in methanol (10 mL)
5. additionTo the solution was added NaBH4 (50 mg) at 0° C.
6. additionThe mixture was poured into saturated aqueous solution of NH4Cl
7. extractionextracted with CHCl3
8. washThe extract was washed with brine
9. dry with materialdried over MgSO4
10. concentrationconcentrated
11. customThe residue was purified with silica gel column chromatography (eluent: hexane/EtOAc=99/1˜1/99)

ORD record

ord-2632f1b507464777b9b472fbb97e8af6

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08263632B2