Water → 1,1-Dimethylethyl 4-(2-propen-1-yl)-4-(2-propen-1-yloxy)-1-piperidinecarboxylate

HRID 2213035Notes

Reaction equation

HRID 2213035 reaction equation
[H-].[Na+].[OH:3][C:4]1([CH2:17][CH:18]=[CH2:19])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.[CH2:20](Br)[CH:21]=[CH2:22].O>CN(C)C=O>[CH2:17]([C:4]1([O:3][CH2:22][CH:21]=[CH2:20])[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[CH2:8][CH2:9]1)[CH:18]=[CH2:19]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 21955339Tert-butyl 4-allyl-4-hydroxypiperidine-1-carboxylate

Product 1

HCID 219552731,1-Dimethylethyl 4-(2-propen-1-yl)-4-(2-propen-1-yloxy)-1-piperidinecarboxylateYield 20.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (60% dispersion in mineral oil, 12 g, 0.3 mol) was added slowly to a stirred, cooled (0° C.) solution of 1,1-dimethylethyl 4-hydroxy-4-(2-propenyl)-1-piperidinecarboxylate (Description 129, 23.1 g, 0.096 mol) in dimethylformamide (200 mL) and the mixture was stirred at 0° C. for 10 minutes. Allyl bromide (25.4 ml, 0.3 mol) was added and the mixture was stirred at 0° C. for 5 minutes, then at room temperature for 45 minutes. The mixture was cooled to 0° C. and water (200 mL) was added. The mixture was extracted with diethyl ether (2×200 mL) and the combined organic fractions were washed with water (4×200 mL) and brine (150 mL), dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with isohexane/EtOAc (9:1), to give the title compound (5.5 g, 20%). m/z (E) 226 (M+1-C4H8).

Workup

  1. stirringthe mixture was stirred at 0° C. for 5 minutes
  2. waitat room temperature for 45 minutes
  3. temperatureThe mixture was cooled to 0° C.
  4. extractionThe mixture was extracted with diethyl ether (2×200 mL)
  5. washthe combined organic fractions were washed with water (4×200 mL) and brine (150 mL)
  6. dry with materialdried (MgSO4)
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by flash column chromatography on silica gel
  9. washeluting with isohexane/EtOAc (9:1)

Sources & evidence

ORD record
ord-d80f647e9b8b4546b533af3322cc84ee
Source dataset
uspto-grants-2006_09
Patent number
US07105507B2

Reaction notes

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