tert-Butyl bromoacetate → 1,1-Dimethylethyl 4-hydroxy-1-piperidineacetate

To a heated (40° C.) solution of tert-butyl 2-bromoacetate (7.38 mL, 49.9 mmol) in THF (10 mL) was added dropwise a solution of piperidin-4-ol (5.050 g, 49.9 mmol) and TEA (6.96 mL, 49.9 mmol) in THF (50 mL). The mixture was refluxed for 2 hours and then cooled to RT and filtered through a pad of Celite® brand filter aid. The filtrate was evaporated and the residue diluted with EtOAc (50 mL), washed with water (50 mL), brine (10 mL), and the organic layer dried over Na2SO4, filtered and evaporated. The material was purified via flash chromatography using a linear gradient of 0% to 10% of 1% NH4OH in MeOH in DCM. The title compound was isolated as an off-white solid (4.865 g, 45% yield).

1. temperatureThe mixture was refluxed for 2 hours
2. filtrationfiltered through a pad of Celite® brand
3. filtrationfilter aid
4. customThe filtrate was evaporated
5. additionthe residue diluted with EtOAc (50 mL)
6. washwashed with water (50 mL), brine (10 mL)
7. dry with materialthe organic layer dried over Na2SO4
8. filtrationfiltered
9. customevaporated
10. customThe material was purified via flash chromatography

ORD record

ord-d38152437bf443e3a488378969c8d923

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09115127B2