Hydrochloric Acid → 1-[(2R*,6S*)-2-(2-fluorophenyl)-6-vinylpiperidin-1-yl]-3-buten-1-one

HRID 553909Notes

Reaction equation

HRID 553909 reaction equation
C(P(=O)(OCC)OCC)#N.[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C@H:18]1[CH2:23][CH2:22][CH2:21][C@@H:20]([CH:24]=[CH2:25])[NH:19]1.[CH:26]([CH2:28][C:29](O)=[O:30])=[CH2:27].Cl>CN(C=O)C.C(OCC)(=O)C.C(N(CC)CC)C>[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C@H:18]1[CH2:23][CH2:22][CH2:21][C@@H:20]([CH:24]=[CH2:25])[N:19]1[C:29](=[O:30])[CH2:28][CH:26]=[CH2:27]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 327433-Butenoic acidHCID 76257Diethyl cyanophosphonateHCID 69077314(2R*,6S*)-2-(2-fluorophenyl)-6-vinylpiperidine

Product 1

HCID 690734691-[(2R*,6S*)-2-(2-fluorophenyl)-6-vinylpiperidin-1-yl]-3-buten-1-one

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Diethyl cyanophosphonate (1.23 mL) was added to a solution of (2R*,6S*)-2-(2-fluorophenyl)-6-vinylpiperidine (518 mg), vinylacetic acid (0.66 mL), and triethylamine (2.1 mL) in DMF (10 mL) at room temperature, and the reaction solution was stirred at room temperature for 21 hours. Ethyl acetate and 1 N hydrochloric acid were added to the reaction solution, and the organic layer was separated. The resulting organic layer was sequentially washed with saturated sodium bicarbonate water and brine, dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 442 mg of the title compound. The property values of the compound are as follows.

Workup

  1. customthe organic layer was separated
  2. washThe resulting organic layer was sequentially washed with saturated sodium bicarbonate water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-659f915a9cd045b9a304f956775a0617
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

Loading…