1-Benzyl-3-pyrrolidinone → 1-Benzyl-3-methylpyrrolidin-3-OL

A solution of 1-benzylpyrrolidin-3-one (9.98 g, 57.0 mmol) in THF (57.0 mL) at −20° C. was added to 1.4M MeMgBr (85.4 mL, 120 mmol). When addition was complete, the ice bath was removed and the reaction was allowed to warm to ambient temperature and then quenched with water (200 mL). The mixture was diluted with saturated NH4Cl (200 mL) and ethyl acetate (300 mL) and stirred vigorously for 5 minutes. An inseparable emulsion formed with fine particulates. The reaction mixture was filtered under vacuum and the layers were separated. The aqueous layer was extracted with ethyl acetate (200 mL) and the organic layer was washed with brine (100 mL), dried (MgSO4), filtered and concentrated under reduced pressure to an oil which was purified by flash chromatography (0-5% Methanol/DCM) to give (+/−)1-benzyl-3-methylpyrrolidin-3-ol (6.10 g, 31.9 mmol, 56.0% yield).

1. additionWhen addition
2. customthe ice bath was removed
3. customquenched with water (200 mL)
4. additionThe mixture was diluted with saturated NH4Cl (200 mL) and ethyl acetate (300 mL)
5. customAn inseparable emulsion formed with fine particulates
6. filtrationThe reaction mixture was filtered under vacuum
7. customthe layers were separated
8. extractionThe aqueous layer was extracted with ethyl acetate (200 mL)
9. washthe organic layer was washed with brine (100 mL)
10. dry with materialdried (MgSO4)
11. filtrationfiltered
12. concentrationconcentrated under reduced pressure to an oil which
13. customwas purified by flash chromatography (0-5% Methanol/DCM)

ORD-Eintrag

ord-fbff5070666d43c089dc2c9a57df141b

Quelldatensatz

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08889704B2