Hydrochloric Acid → HCID 67490886, compound

Temperature

55 °C

(3S,4S)-3-Allyl-4-(tert-butyldimethylsilyloxy)methyl-1-[(1R)-1-phenylethyl]pyrrolidine (213 g, 592 mmol) was dissolved in dichloromethane (420 mL). Benzyl chloroformate (169.2 mL, 1.19 mol) was added dropwise, and the mixture was stirred at 55° C. for 10 hours and then at room temperature for 14 hours. A 1 M solution of hydrochloric acid in ethanol (250 mL, 250 mmol) was further added to the reaction solution, and the mixture was stirred at room temperature for 24 hours. The reaction solution was extracted with a saturated sodium bicarbonate solution and ethyl acetate. Then, the organic layer was washed with brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1→1:1) to give 140 g of the title compound as a pale yellow oil.

1. waitat room temperature for 14 hours
2. stirringthe mixture was stirred at room temperature for 24 hours
3. extractionThe reaction solution was extracted with a saturated sodium bicarbonate solution and ethyl acetate
4. washThen, the organic layer was washed with brine
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1→1:1)

ORD record

ord-355613355dae4783b5374b27964989fe

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08618094B2