Sodium Bicarbonate → 1-Benzyl-3,3-difluoropiperidine-4,4-diol

HRID 2035636ノート

反応式

HRID 2035636 の反応式
[CH2:1]([N:8]1[CH2:13][C:12]([F:15])([F:14])[C:11](=[O:16])[CH:10](C(OCC)=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(O)=[O:23].[Na+]>Cl>[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 2

HCID 516892Sodium BicarbonateHCID 49761228Ethyl 1-benzyl-5,5-difluoro-4-oxopiperidine-3-carboxylate

生成物 1

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

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

Ethyl 1-benzyl-5,5-difluoro-4-oxopiperidine-3-carboxylate (6.00 g, 20.2 mmol; prepared as described in WO 2005/040120, p. 30) was dissolved in 3N HCl (60 mL) and heated to reflux for 16 hours. The reaction was cooled, adjusted to pH 8 with solid NaHCO3, then extracted three times with ethyl acetate. The combined organics were washed with saturated NaCl, dried over Na2SO4 and concentrated in vacuo to a white solid (5.1 g). MS APCI (+) m/z 244.0 (M+1) detected.

後処理

  1. temperatureheated
  2. temperatureto reflux for 16 hours
  3. temperatureThe reaction was cooled
  4. extractionextracted three times with ethyl acetate
  5. washThe combined organics were washed with saturated NaCl
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo to a white solid (5.1 g)

出典と根拠

ORDレコード
ord-c44c8a181edc4719bbcb61d2e2cc431c
出典データセット
uspto-grants-2013_11
特許番号
US08575145B2

反応ノート

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