Ammonium Chloride → 863111-06-2

HRID 1670760ノート

反応式

HRID 1670760 の反応式
C(OC([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)=O)(C)(C)C.[F:15][C:16]1[CH:17]=[C:18]([Mg]Br)[CH:19]=[CH:20][CH:21]=1.[Cl-:24].[NH4+]>O1CCCC1>[ClH:24].[F:15][C:16]1[CH:21]=[C:20]([C:11]2([OH:14])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:19]=[CH:18][CH:17]=1

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 178505773HCID 178505773、化合物

生成物 1

HCID 23149879863111-06-2収率 35%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

1-(tert-Butoxycarbonyl)-4-piperidone (2.19 g) was dissolved in tetrahydrofuran (30 ml) and the mixture was cooled to 0° C. 3-Fluorophenylmagnesiumbromide (Tokyo Chemical Industry CO., LTD., 1M, 13.2 ml) was added and the mixture was stirred for 6 hr. After completion of the reaction, a saturated aqueous ammonium chloride solution was added, and the mixture was extracted three times with ethyl acetate. The organic layer was dried and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (elution solvent: hexane-ethyl acetate (5:1-2:1)). Then, 4N hydrochloric acid-ethyl acetate (10 ml) was added and the mixture was stirred for 3 hr. Diethyl ether was added and the precipitated solid was collected by filtration to give 4-(3-fluorophenyl)piperidin-4-ol hydrochloride (902 mg, yield 35%).

後処理

  1. customAfter completion of the reaction
  2. extractionthe mixture was extracted three times with ethyl acetate
  3. customThe organic layer was dried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (elution solvent: hexane-ethyl acetate (5:1-2:1))
  6. additionThen, 4N hydrochloric acid-ethyl acetate (10 ml) was added
  7. stirringthe mixture was stirred for 3 hr
  8. additionDiethyl ether was added
  9. filtrationthe precipitated solid was collected by filtration

出典と根拠

ORDレコード
ord-4facead53c424ac6aa79e676eba4397a
出典データセット
uspto-grants-2011_08
特許番号
US07994196B2

反応ノート

読み込み中…