Benzyl Bromide → HCID 86612400, compound

Temperature

0 °C

Sodium hydride (60% dispersion in mineral oil, 2.13 g, 53.41 mmol) was added portionwise to an ice-cooled solution of (S)-(−)-N-boc-3-pyrrolidinol (10 g, 53.41 mmol) in tetrahydrofuran (100 mL) and the mixture was stirred at 0° C. for 1 hour. Benzyl bromide (6.4 mL, 53.41 mmol) and tetrahydrofuran (50 mL) were added and the mixture was stirred for 6 hours allowing the temperature to rise to 25° C. The reaction mixture was then slowly diluted with water (50 mL), concentrated in vacuo and the aqueous residue was extracted with ethyl acetate (3×70 mL). The combined organic solution was washed with brine (30 mL), dried over sodium sulfate and concentrated in vacuo to give an orange oil. This oil was purified by column chromatography on silica gel, eluting with dichloromethane:methanol:0.88 ammonia, 100:0:0 to 90:10:1. The appropriate fractions were evaporated under reduced pressure and the residue was further purified by column chromatography on silica gel, eluting with pentane:ethyl acetate, 66:33, to afford the title compound as a colourless oil in 74% yield, 10.93 g.

1. stirringthe mixture was stirred for 6 hours
2. customto rise to 25° C
3. concentrationconcentrated in vacuo
4. extractionthe aqueous residue was extracted with ethyl acetate (3×70 mL)
5. washThe combined organic solution was washed with brine (30 mL)
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated in vacuo
8. customto give an orange oil
9. customThis oil was purified by column chromatography on silica gel
10. washeluting with dichloromethane
11. customThe appropriate fractions were evaporated under reduced pressure
12. customthe residue was further purified by column chromatography on silica gel
13. washeluting with pentane

ORD record

ord-f07609111bd74a77b4969f5cb2486f66

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08268881B2