反应详情

Methylmagnesium chloride (9.53 mL, 3.0M tetrahydrofuran solution) was added to tetrahydrofuran (45.5 mL). Benzyl 4-oxopiperidine-1-carboxylate (5.00 g) was dissolved in tetrahydrofuran (8.8 mL), and added dropwise to a solution of ice-cooled methylmagnesium chloride in tetrahydrofuran, and the mixture was stirred at room temperature for 14 hr. The reaction mixture was ice-cooled, aqueous ammonium chloride solution (ammonium chloride 1.41 g, water 15 mL) was added dropwise, and the mixture was partitioned and extracted with ethyl acetate. The aqueous layer was extracted with ethyl acetate, and the combined organic layer was dried over magnesium sulfate, and purified by NH-silica gel column chromatography [developing solvent; hexane:ethyl acetate=80:20 (volume ratio)→60:40 (volume ratio)]. The obtained solid was washed with isopropyl ether, and dried under reduced pressure to give the title compound (4.20 g, yield 79%) as a colorless solid.

1. additionadded dropwise to a solution of ice-
2. temperaturecooled
3. customthe mixture was partitioned
4. extractionextracted with ethyl acetate
5. extractionThe aqueous layer was extracted with ethyl acetate
6. dry with materialthe combined organic layer was dried over magnesium sulfate
7. custompurified by NH-silica gel column chromatography [
8. washThe obtained solid was washed with isopropyl ether
9. customdried under reduced pressure