tert-Butyl 4-(2-bromoethyl)piperidine-1-carboxylate → tert-Butyl 4-ethenylpiperidine-1-carboxylate

HRID 343403Notes

Reaction equation

HRID 343403 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15]Br)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]=[CH2:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 10541625tert-Butyl 4-(2-bromoethyl)piperidine-1-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 10910832tert-Butyl 4-ethenylpiperidine-1-carboxylateYield 63.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4(2-bromo-ethyl)-piperidine-1-carboxylic acid tert-butyl ester (81.5 g 0.279 mol) in dry tetrahydrofuran (1000 ml) under nitrogen at 20° was treated portionwise, over 30 min, with potassium tert-butoxide (63.2 g 0.563 mol). The mixture was stirred at 25° for 3 h and partitioned between saturated aqueous ammonium chloride (1000 ml) and diethyl ether (500 ml). The aqueous phase was extracted with diethyl ether (4×500 ml) and the combined, dried (MgSO4) extracts were evaporated in vacuo. The residue was purified by flash column chromatography on silica gel (Merck 9385) eluant cyclohexane: diethyl ether (19:1) to give the title compound as an orange oil (37.1 g, 0.176 mol, 63%).

Workup

  1. custompartitioned between saturated aqueous ammonium chloride (1000 ml) and diethyl ether (500 ml)
  2. extractionThe aqueous phase was extracted with diethyl ether (4×500 ml)
  3. dry with materialdried (MgSO4) extracts
  4. customwere evaporated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel (Merck 9385) eluant cyclohexane: diethyl ether (19:1)

Sources & evidence

ORD record
ord-037bf861cbb841c4af6f44ba23b9e542
Source dataset
uspto-grants-1999_01
Patent number
US05861414

Reaction notes

Loading…