Allyl bromide → Tert-butyl 4-allyl-4-hydroxypiperidine-1-carboxylate

To a solution of tert-butyl 4-oxopiperidine-1-carboxylate (10 g, 50.2 mmol), allyl bromide (10.8 mL, 124 mmol) in THF (10 mL), and saturated ammonium chloride solution (50 mL) was added Zn dust (6.5 g, 100 mmol) portionwise below 10° C. After addition was complete, the reaction mixture was stirred overnight, when TLC indicated consumption of s.m. The reaction mixture was diluted with water (50 mL) and acidified with several drops of 10% H2SO4 to pH=6. The reaction mixture was extracted with EtOAc (3×200 mL), The organic layers were combined and washed with a saturated solution of NaHCO3, brine and evaporated, to give the crude product which was purified by chromatography to give title compound 11B as colorless oil.

1. additionAfter addition
2. customconsumption of s.m
3. additionThe reaction mixture was diluted with water (50 mL)
4. extractionThe reaction mixture was extracted with EtOAc (3×200 mL)
5. washwashed with a saturated solution of NaHCO3, brine
6. customevaporated
7. customto give the crude product which
8. customwas purified by chromatography

ORD record

ord-b050d44a0dd44777915013637ead0224

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09108921B2