Sodium Chloride → (3R,4R)-3-azidomethyl-1-benzyloxycarbonyl-4-hydroxypyrrolidine

(3R,4R)-3-Azidomethyl-1-benzyloxycarbonyl-4-(tert-butyldimethylsilyl)oxypyrrolidine (3.05 g) was dissolved in tetrahydrofuran (50 mL). While this solution was cooled on an ice bath, tetrabutylammonium fluoride (lmol/L tetrahydrofuran solution, 13.3 mL) was added dropwise and the mixture was stirred for additional 1 hour. Subsequently, a saturated aqueous solution of sodium chloride 70 mL) was added and the mixture was extracted with ethyl acetate (150 mL, 100 mL). The ethyl acetate extracts were combined and the combined solvent was dried over anhydrous sodium sulfate and was concentrated under reduced pressure. The resulting residue was purified on a silica gel column (eluant=ethyl acetate) to give 2.01 g of (3R,4R)-3-azidomethyl-1-benzyloxycarbonyl-4-hydroxypyrrolidine as a milky white syrup-like product.

1. temperatureWhile this solution was cooled on an ice bath
2. extractionthe mixture was extracted with ethyl acetate (150 mL, 100 mL)
3. dry with materialthe combined solvent was dried over anhydrous sodium sulfate
4. concentrationwas concentrated under reduced pressure
5. customThe resulting residue was purified on a silica gel column (eluant=ethyl acetate)

ORD record

ord-a36ca6eb86fa417aa83366291412673c

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07153851B2