Hydrochloric Acid → 1-[(2R*,6S*)-2-(4-fluorophenyl)-6-vinylpiperidin-1-yl]-3-buten-1-one

HRID 553854노트

반응식

HRID 553854 반응식
C(P(=O)(OCC)OCC)#N.[F:11][C:12]1[CH:17]=[CH:16][C:15]([C@H:18]2[CH2:23][CH2:22][CH2:21][C@@H:20]([CH:24]=[CH2:25])[NH:19]2)=[CH:14][CH:13]=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]=[CH:14][C:15]([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:16][CH:17]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 327433-Butenoic acidHCID 76257Diethyl cyanophosphonateHCID 69010346(2R*,6S*)-2-(4-fluorophenyl)-6-vinylpiperidine

생성물 1

HCID 690774971-[(2R*,6S*)-2-(4-fluorophenyl)-6-vinylpiperidin-1-yl]-3-buten-1-one

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

Diethyl cyanophosphonate (2.1 mL) was added to a solution of (2R*,6S*)-2-(4-fluorophenyl)-6-vinylpiperidine (934 mg), vinylacetic acid (1.15 mL), and triethylamine (3.82 mL) in DMF (10 mL), and the reaction solution was stirred at room temperature for six hours. Ethyl acetate and 1 N aqueous hydrochloric acid were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with saturated sodium bicarbonate water, dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane->heptane:ethyl acetate=1:1) to obtain 744 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 washed with saturated sodium bicarbonate water
  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->heptane:ethyl acetate=1:1)

출처 및 근거

ORD 기록
ord-53b606dbcc1c4c498825f28e6a468b89
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08048878B2

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