Water → HCID 12148215, compound

HRID 1501889Notes

Reaction equation

HRID 1501889 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.[CH:15]([Mg]Br)=[CH2:16].O>ClCCl>[CH:15]([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)=[CH2:16]

Participants

5

Reactant 3

HCID 962WaterHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 178418507HCID 178418507, compound

Product 1

HCID 12148215HCID 12148215, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-oxopiperidine-1-carboxylate (1.00 g, 5.02 mmol) in 20 mL of dichloromethane at 0° C. under an atmosphere of nitrogen was added vinylmagnesium bromide (0.7 M dichloromethane solution, 9.32 mL, 6.52 mmol) dropwise. After 1 hr, the mixture was treated with water and extracted 3× with ethyl acetate. The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 0-60% ethyl acetate in hexanes, to provide tert-butyl 4-ethenyl-4-hydroxypiperidine-1-carboxylate that gave a proton NMR spectra consistent with theory.

Workup

  1. extractionextracted 3× with ethyl acetate
  2. dry with materialThe combined organic extracts were dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified via silica gel chromatography
  6. washeluting with 0-60% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-d7ce98ae62bc4eae9fbeabbc3cd5a20f
Source dataset
uspto-grants-2015_12
Patent number
US09206200B2

Reaction notes

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