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

HRID 553903노트

반응식

HRID 553903 반응식
C(P(=O)(OCC)OCC)#N.[F:11][C:12]1[CH:13]=[C:14]([C@H:18]2[CH2:23][CH2:22][CH2:21][C@@H:20]([CH:24]=[CH2:25])[NH:19]2)[CH:15]=[CH:16][CH:17]=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:13]=[C:14]([C@H:18]2[CH2:23][CH2:22][CH2:21][C@@H:20]([CH:24]=[CH2:25])[N:19]2[C:29](=[O:30])[CH2:28][CH:26]=[CH2:27])[CH:15]=[CH:16][CH:17]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 327433-Butenoic acidHCID 76257Diethyl cyanophosphonateHCID 69073751(2R*,6S*)-2-(3-fluorophenyl)-6-vinylpiperidine

생성물 1

HCID 690769341-[(2R*,6S*)-2-(3-fluorophenyl)-6-vinylpiperidin-1-yl]-3-buten-1-one

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

Diethyl cyanophosphonate (1.78 mL) was added to a solution of (2R*,6S*)-2-(3-fluorophenyl)-6-vinylpiperidine (748 mg), vinylacetic acid (0.96 mL), and triethylamine (3.1 mL) in DMF (15 mL) at room temperature, and the reaction solution was stirred at room temperature for 27 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 587 mg of the title compound. The property values of the compound are as follows.

후처리

  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)

출처 및 근거

ORD 기록
ord-1c1b8e30beca4ec0a1c200602cf79875
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08048878B2

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