Pyridine → Ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-chlorobutyrate

HRID 280972노트

반응식

HRID 280972 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH:19](O)[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.S(Cl)([Cl:34])=O>O.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH:19]([Cl:34])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 20143718Ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-hydroxybutyrate

생성물 1

HCID 20143712Ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-chlorobutyrate

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매2회

실험 절차

To a mixture of ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-hydroxybutyrate (11.5 g), ethyl acetate (200 ml) and pyridine (12 g) is added thionyl chloride (5 ml), and the resulting mixture is refluxed for 1 hour with stirring. After cooling, the mixture is diluted with water (500 ml) and ethyl acetate (100 ml). The organic layer is separated, washed successively with 0.1N hydrochloric acid and water, dried over anhydrous magnesium sulfate, treated with activated carbon and then evaporated in vacuo to give ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-chlorobutyrate (10.5 g) as a pale yellow oil.

후처리

  1. temperaturethe resulting mixture is refluxed for 1 hour
  2. temperatureAfter cooling
  3. customThe organic layer is separated
  4. washwashed successively with 0.1N hydrochloric acid and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. additiontreated with activated carbon
  7. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-aedfb4bc06314ea98089d8adc5d09429
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04591458

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