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

HRID 540406노트

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HRID 540406 반응식
[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]

참가 물질

5

반응물 3

HCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 65920243HCID 65920243, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
0 °C

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-b43867cb141840adb265b09dec1950eb
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871187B2

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