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

HRID 553877
ノート
印刷プレビュー

反応式

HRID 553877 の反応式
C(P(=O)(OCC)OCC)#N.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C@H:19]2[CH2:24][CH2:23][CH2:22][C@@H:21]([CH:25]=[CH2:26])[NH:20]2)=[CH:15][CH:14]=1.[CH:27]([CH2:29][C:30](O)=[O:31])=[CH2:28].Cl>CN(C=O)C.C(OCC)(=O)C.C(N(CC)CC)C>[CH3:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([C@H:19]2[CH2:24][CH2:23][CH2:22][C@@H:21]([CH:25]=[CH2:26])[N:20]2[C:30](=[O:31])[CH2:29][CH:27]=[CH2:28])=[CH:17][CH:18]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 327433-Butenoic acidHCID 76257Diethyl cyanophosphonateHCID 69069541(2R*,6S*)-2-(4-methoxyphenyl)-6-vinylpiperidine

生成物 1

HCID 690748621-[(2R*,6S*)-2-(4-methoxyphenyl)-6-vinylpiperidin-1-yl]-3-buten-1-one

試薬・触媒・溶媒 3

HCID 6228
Dimethylformamide
溶媒
HCID 8471Triethylamine溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

Diethyl cyanophosphonate (0.67 mL) was added to a solution of (2R*,6S*)-2-(4-methoxyphenyl)-6-vinylpiperidine (320 mg), vinylacetic acid (0.37 mL), and triethylamine (1.23 mL) in DMF (5 mL), and the reaction solution was stirred at room temperature for nine 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 100 mg of the title compound. The property value of the compound is as follows.

後処理

  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)

出典と根拠

ORDレコード
ord-d40836c90a1e41a0b06b1275bc50066d
出典データセット
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08048878B2

反応ノート

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