Hydrochloric Acid → 1-Benzyl-3,3-difluoropiperidine-4,4-diol

HRID 2206263ノート

反応式

HRID 2206263 の反応式
[CH2:1]([N:8]1[CH2:13][C:12]([F:15])([F:14])[C:11]([OH:16])=[C:10](C(OCC)=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[O:23]1CCOCC1>>[CH2:1]([N:8]1[CH2:9][CH2:10][C:11]([OH:16])([OH:23])[C:12]([F:14])([F:15])[CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67343743Ethyl 1-benzyl-5,5-difluoro-4-hydroxy-1,2,5,6-tetrahydropyridine-3-carboxylate

生成物 1

HCID 574158661-Benzyl-3,3-difluoropiperidine-4,4-diol

反応条件

温度
80 °C

実験手順

A mixture of ethyl 1-benzyl-5,5-difluoro-4-hydroxy-1,2,5,6-tetrahydropyridine-3-carboxylate (5.0 g) and conc. hydrochloric acid (40 mL) in 1,4-dioxane (15 mL) was stirred at 80° C. for 3 hr. The reaction mixture was concentrated under reduced pressure, and diluted with ethyl acetate, and the mixture was adjusted to pH-9 with saturated aqueous sodium carbonate solution. The aqueous layer was extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was washed with dichloromethane to give the title compound (1.40 g).

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with ethyl acetate
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washThe residue was washed with dichloromethane

出典と根拠

ORDレコード
ord-269f23fdeb6f4e689d03b04e158a7fcd
出典データセット
uspto-grants-2016_06
特許番号
US09371320B2

反応ノート

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