tert-Butyl 3,3-dimethyl-4-oxopiperidine-1-carboxylate → 4-(4-Chloro-phenyl)-4-hydroxy-3,3-dimethyl-piperidine-1-carboxylic acid tert-butyl ester

HRID 242562

반응식

HRID 242562 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[C:10]([CH3:16])([CH3:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([Mg]Br)=[CH:20][CH:19]=1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:21]2[CH:22]=[CH:23][C:18]([Cl:17])=[CH:19][CH:20]=2)([OH:14])[C:10]([CH3:16])([CH3:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

4

반응물 2

HCID 22278899tert-Butyl 3,3-dimethyl-4-oxopiperidine-1-carboxylateHCID 178478191HCID 178478191, 화합물

생성물 1

HCID 593412124-(4-Chloro-phenyl)-4-hydroxy-3,3-dimethyl-piperidine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To an ice-cooled solution 3,3-Dimethyl-4-oxo-piperidine-1-carboxylic acid tert-butyl ester (1.6 g, 7.2 mmol) in THF (20 mL) was added 4-chlorophenylmagnesium bromide (1 M in ether, 15 mL, 15 mmol). The solution was allowed to warm to about room temperature, then stirred at room temperature for about 22 hours. The reaction was quenched with aqueous ammonium chloride and extracted with ethyl acetate. The combined organic layers were concentrated in vacuo, then purified by flash chromatography on silica gel (35 g SiO2, gradient elution from 100% hexane to 100% ethyl acetate) to yield the title compound as a colorless oil.

후처리

  1. temperatureto warm to about room temperature
  2. customThe reaction was quenched with aqueous ammonium chloride
  3. extractionextracted with ethyl acetate
  4. concentrationThe combined organic layers were concentrated in vacuo
  5. custompurified by flash chromatography on silica gel (35 g SiO2, gradient elution from 100% hexane to 100% ethyl acetate)

출처 및 근거

ORD 기록
ord-78bdd389d3534e50b6c0cd096fb8ef8e
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653096B2

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