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Ethyl diazoacetate → Ethyl 2-((S)-2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-2-oxopiperidin-1-yl)butoxy)acetate

HRID 1048211
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HRID 1048211 반응식
[CH2:1]([C@H:4]1[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:6]([C@@H:24]([CH2:30][CH3:31])[C:25](OCC)=[O:26])[C:5]1=[O:32])[CH:2]=[CH2:3].[N+](=[CH:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[N-]>C(Cl)Cl.C([O-])(=O)C.[Rh+2].C([O-])(=O)C>[CH2:1]([C@H:4]1[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:6]([C@@H:24]([CH2:30][CH3:31])[CH2:25][O:26][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[C:5]1=[O:32])[CH:2]=[CH2:3]
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참가 물질

5

반응물 2

HCID 12192Ethyl diazoacetateHCID 60154134(S)-Ethyl 2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-2-oxopiperidin-1-yl)butanoate

생성물 1

HCID 58573922Ethyl 2-((S)-2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-2-oxopiperidin-1-yl)butoxy)acetate

시약·촉매·용매 2

HCID 21674Acetic acid, rhodium(2+) salt촉매
HCID 6344
Dichloromethane
용매

반응 조건

온도
25 °C

실험 절차

To a solution of 203 mg (0.47 mmol) of (3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-hydroxybutan-2-yl)piperidin-2-one (Example 9, Step B) and rhodium(II)acetate dimmer (10.4 mg, 0.047 mmol) in CH2Cl2 (1.90 mL) was added dropwise ethyl diazoacetate (286 μL, 2.35 mmol) at 25° C. After being stirred at 25° C. for 14 h, the reaction was concentrated under reduced pressure and purified by chromatography on silica gel (20% to 30% EtOAc/Hexanes, gradient elution) to provide the title compound as a colorless liquid:

후처리

  1. concentrationthe reaction was concentrated under reduced pressure
  2. custompurified by chromatography on silica gel (20% to 30% EtOAc/Hexanes, gradient elution)

출처 및 근거

ORD 기록
ord-07b7320210be48369deb3e401cade490
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08569341B2

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