Allyl bromide → Tert-butyl 4-(allyloxy)piperidine-1-carboxylate

HRID 265887Notes

Reaction equation

HRID 265887 reaction equation
[H-].[Na+].[C:3]([N:10]1[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]1)([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[CH2:17](Br)[CH:18]=[CH2:19]>CN(C=O)C>[C:3]([N:10]1[CH2:15][CH2:14][CH:13]([O:16][CH2:19][CH:18]=[CH2:17])[CH2:12][CH2:11]1)([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 21990010Tert-butyl 4-(allyloxy)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of NaH (0.48 g, 11.9 mmol; 60% dispersion) in dry DMF (50 mL) at 0° C. was added a solution of 21-2 (2.0 g, 9.9 mmol) in DMF (15 mL). After 10 min, the cooling bath was removed, but then returned after another 10 min, followed by addition of allyl bromide (4.3 mL, 50 mmol). After 1.5 h, the reaction was quenched with 10% KHSO4 and then diluted with H2O (90 mL). The reaction mixture was extracted with EtOAc, the layers separated, and the EtOAc portion washed with H2O, 5% KHSO4, sat. NaHCO3 and brine, dried (MgSO4) and concentrated. Flash chromatography (silica, 20% EtOAc/hexanes) gave 21-3 as a yellowish oil. Rf 0.47 (silica, 20% EtOAc/hexanes).

Workup

  1. customthe cooling bath was removed
  2. waitreturned after another 10 min
  3. waitAfter 1.5 h
  4. customthe reaction was quenched with 10% KHSO4
  5. additiondiluted with H2O (90 mL)
  6. extractionThe reaction mixture was extracted with EtOAc
  7. customthe layers separated
  8. washthe EtOAc portion washed with H2O, 5% KHSO4, sat. NaHCO3 and brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-03e07536c7d9450ab30debdfac6fac54
Source dataset
uspto-grants-1997_07
Patent number
US05648368

Reaction notes

Loading…