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

HRID 2202340Notes

Reaction equation

HRID 2202340 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH2:15](Br)[CH:16]=[CH2:17].[Cl-].[NH4+]>C1COCC1.[Zn]>[CH2:17]([C:2]1([OH:1])[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1)[CH:16]=[CH2:15]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 25517Ammonium ChlorideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 21955339Tert-butyl 4-allyl-4-hydroxypiperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8137ed892ce849ea8f8a22eb48be07e0
Source dataset
uspto-grants-2016_06
Patent number
US09365545B2

Reaction notes

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