Water → tert-Butyl 4-(cyanomethyl)piperidine-1-carboxylate

HRID 1616075ノート

反応式

HRID 1616075 の反応式
CS(O[CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1)(=O)=O.O.[C-:21]#[N:22].[Na+]>C(O)C>[C:21]([CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1)#[N:22]

参加物

5

反応物 3

HCID 962WaterHCID 8929Sodium CyanideHCID 2765838Tert-butyl 4-(methylsulfonyloxymethyl)piperidine-1-carboxylate

生成物 1

HCID 22248390tert-Butyl 4-(cyanomethyl)piperidine-1-carboxylate収率 77%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

tert-Butyl 4-{[(methylsulfonyl)oxy]methyl}piperidine-1-carboxylate (15.3 g) was dissolved in ethanol (80 mL), water (20 mL) and sodium cyanide (4.0 g, 80 mmol) were added, and stirring was conducted at 80° C. for 24 hours. Ethanol was distilled off, water and ethyl acetate were added, and then the resultant mixture was subject to Celite filtration, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under a reduced pressure, and the obtained residue was purified by using silica gel column chromatography (hexane:ethyl acetate=3:1→2:1) to give tert-butyl 4-(cyanomethyl)piperidine-1-carboxylate (6.87 g, 77%, 3 steps) as a white solid.

後処理

  1. distillationEthanol was distilled off
  2. additionwater and ethyl acetate were added
  3. filtrationthe resultant mixture was subject to Celite filtration
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under a reduced pressure
  8. customthe obtained residue was purified

出典と根拠

ORDレコード
ord-4a8eef4698b24512b037e2164243767f
出典データセット
uspto-grants-2014_07
特許番号
US08765771B2

反応ノート

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