Allyl bromide → 1-tert-Butyl 4-methyl 4-allylpiperidine-1,4-dicarboxylate

Temperatur

0 °C

To a −78° C. solution of N-Boc-4-piperidinecarboxylic acid methyl ester (5.70 g, 23.4 mmol) in THF (80 mL) was added potassium hexamethyldisilazide (0.5 M in toluene, 70.2 mL, 35.1 mmol). After 2 h allyl bromide (6.69 mL, 77.3 mmol) was added, the reaction stirred at this temperature for 0.5 h, then warmed to 0° C. After 3 h the reaction was quenched by the addition of saturated aqueous ammonium chloride and extracted with dichloromethane (3×). The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of 0 to 8% methanol:dichloromethane to give the title compound (6.0 g). MS: m/z=284.2 (M+1).

1. customAfter 3 h the reaction was quenched by the addition of saturated aqueous ammonium chloride
2. extractionextracted with dichloromethane (3×)
3. dry with materialThe combined organic layers were dried over MgSO4
4. filtrationfiltered
5. concentrationconcentrated under reduced pressure
6. customThe crude product was purified by silica gel chromatography
7. washeluting with a gradient of 0 to 8% methanol

ORD-Eintrag

ord-b68e3a2888eb44f28e14a22b93b3eae6

Quelldatensatz

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07659264B2