Benzyl 4-oxopiperidine-1-carboxylate → HCID 58562578, compound

Temperature

-78 °C

Into a 100 mL 3-necked round-bottom flask, was placed a solution of 2-(tert-butyldimethylsilyl)thiazole (1.58 g, 7.94 mmol, 1.00 equiv) in tetrahydrofuran (40 mL). This was followed by the addition of n-BuLi (3.7 mL, 1.20 equiv) dropwise with stirring at −78° C. in 1 hr. After half-hour, the benzyl 4-oxopiperidine-1-carboxylate (1.85 g, 7.94 mmol, 1.00 equiv) was added dropwise with stirring at −78° C. in 0.5 hr. The reaction mixture was stirred for 2 h at −78° C. in a liquid nitrogen bath. The reaction was then quenched by the addition of 50 mL of water. The resulting solution was extracted with 3×100 mL of ethyl acetate, and the combined organic layers washed with 2×100 mL of brine, dried (Na2SO4), and concentrated under vacuum. The residue was purified by chromatography over a silica gel column with ethyl acetate/petroleum ether (1:20-1:1). This resulted in 2 g (58%) of benzyl 4-(2-(tert-butyldimethylsilyl)thiazol-5-yl)-4-hydroxypiperidine-1-carboxylate as yellow oil.

1. customInto a 100 mL 3-necked round-bottom flask, was placed
2. waitAfter half-hour
3. stirringwith stirring at −78° C. in 0.5 hr
4. stirringThe reaction mixture was stirred for 2 h at −78° C. in a liquid nitrogen bath
5. customThe reaction was then quenched by the addition of 50 mL of water
6. extractionThe resulting solution was extracted with 3×100 mL of ethyl acetate
7. washthe combined organic layers washed with 2×100 mL of brine
8. dry with materialdried (Na2SO4)
9. concentrationconcentrated under vacuum
10. customThe residue was purified by chromatography over a silica gel column with ethyl acetate/petroleum ether (1:20-1:1)
11. customThis resulted in 2 g (58%) of benzyl 4-(2-(tert-butyldimethylsilyl)thiazol-5-yl)-4-hydroxypiperidine-1-carboxylate as yellow oil

ORD record

ord-56982543df994b4baa66e8e5d26a2e87

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08518969B2