Hydrochloric Acid → HCID 68862736, compound

To a solution of tert-butyl (3S)-4-hydroxy-3-methyl-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate (1.49 g, 4.88 mmol) in ethanol (30 mL), 1N hydrochloric acid (5.12 mL, 5.12 mmol) was added at room temperature, and the mixture was stirred at 10 minutes. 10% palladium-carbon catalyst (1.40 g) was added to the reaction mixture, and the suspension was stirred in an oil bath at 40° C. for 2 hours in hydrogen atmosphere at normal pressure. After filtering the reaction mixture and concentrating the filtrate, tetrahydrofuran (20 mL), water (20 mL), and sodium hydrogencarbonate (2.05 g, 24.4 mmol) were added to the residue, and benzyloxycarbonyl chloride (836 μl, 5.86 mmol) was further added in an ice bath. The reaction mixture was stirred at room temperature for 2 hours, and extracted with ethyl acetate (100 mL×2). The resulting organic layer was washed with saturated aqueous solution of sodium chloride (20 mL), and dried with anhydrous sodium sulfate. After the filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate, 2:1→1:2) to obtain 1.48 g (90%) of the title compound as a colorless oily substance.

1. filtrationAfter filtering the reaction mixture
2. additionwas further added in an ice bath
3. stirringThe reaction mixture was stirred at room temperature for 2 hours
4. extractionextracted with ethyl acetate (100 mL×2)
5. washThe resulting organic layer was washed with saturated aqueous solution of sodium chloride (20 mL)
6. dry with materialdried with anhydrous sodium sulfate
7. filtrationAfter the filtration
8. concentrationthe filtrate was concentrated under reduced pressure
9. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate, 2:1→1:2)

ORD record

ord-55789cb9052542159f383f190823e81f

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476429B2