Butyl iodide → 1,1-Dimethylethyl 3-butoxy-3-(2-fluorophenyl)-1-azetidinecarboxylate

HRID 540406ノート

反応式

HRID 540406 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([OH:19])[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9]1.[H-].[Na+].I[CH2:23][CH2:24][CH2:25][CH3:26]>CN(C)C=O>[CH2:23]([O:19][C:8]1([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[CH2:9][N:10]([C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])[CH2:11]1)[CH2:24][CH2:25][CH3:26]

参加物

5

反応物 3

HCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 65920243HCID 65920243、化合物

生成物 1

HCID 669889981,1-Dimethylethyl 3-butoxy-3-(2-fluorophenyl)-1-azetidinecarboxylate収率 80.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

135 mg (0.4 mmol) of 3-(2-fluorophenyl)-3-hydroxy-1-(tert-butoxycarbonyl)azetidine at 80% in 2 ml of dimethylformamide are added to a suspension of 65 mg (1.6 mmol) of sodium hydride at 60% in 1.5 ml of dimethylformamide, under nitrogen, at 0° C. After stirring for 20 minutes at 0° C., 0.2 ml (1.5 mmol) of iodobutane are added. The reaction medium is stirred at ambient temperature for 1 h 30 and is then hydrolysed with water and with a saturated aqueous solution of ammonium chloride and extracted with a 1/2 heptane/ethyl acetate mixture. The organic phases are combined, washed with water, dried over magnesium sulphate, filtered and evaporated. The crude product is purified by silica gel chromatography, elution being carried out with an 8/2 heptane/ethyl acetate mixture. 104 mg of 3-butoxy-3-(2-fluorophenyl)-1-(tert-butoxycarbonyl)azetidine are obtained in the form of a yellow oil with a yield of 79%.

後処理

  1. stirringThe reaction medium is stirred at ambient temperature for 1 h 30
  2. extractionhydrolysed with water and with a saturated aqueous solution of ammonium chloride and extracted with a 1/2 heptane/ethyl acetate mixture
  3. washwashed with water
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product is purified by silica gel chromatography, elution

出典と根拠

ORDレコード
ord-b43867cb141840adb265b09dec1950eb
出典データセット
uspto-grants-2014_10
特許番号
US08871187B2

反応ノート

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