Trioxobis(pyridine)chromium → 5-[3-Methoxy-2-(2-methoxycarbonylethyl)-6-pyridyl]-5-oxopentanoic acid methyl ester

HRID 55282

반응식

HRID 55282 반응식
O=[Cr](=O)=O.C1C=CC=CN=1.C1C=CC=CN=1.[CH3:17][O:18][C:19](=[O:39])[CH2:20][CH2:21][CH2:22][CH:23]([C:25]1[N:30]=[C:29]([CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])[C:28]([O:37][CH3:38])=[CH:27][CH:26]=1)[OH:24]>ClCCl.CCCCCC>[CH3:17][O:18][C:19](=[O:39])[CH2:20][CH2:21][CH2:22][C:23]([C:25]1[N:30]=[C:29]([CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])[C:28]([O:37][CH3:38])=[CH:27][CH:26]=1)=[O:24]

참가 물질

5

반응물 2

HCID 88565Trioxobis(pyridine)chromiumHCID 677038195-[3-methoxy-2-(2-methoxycarbonylethyl)-6-pyridyl]-(5RS)-5-hydroxypentanoic acid methyl ester

생성물 1

HCID 541510355-[3-Methoxy-2-(2-methoxycarbonylethyl)-6-pyridyl]-5-oxopentanoic acid methyl ester수율 72.1%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8058Hexane용매

실험 절차

2.9 g of Collins reagent is added to a solution of 470 mg of 5-[3-methoxy-2-(2-methoxycarbonylethyl)-6-pyridyl]-(5RS)-5-hydroxypentanoic acid methyl ester in 50 ml of dichloromethane under argon atmosphere at 0° C., and the mixture is stirred for 2 hours at room temperature. Then, it is diluted with hexane, mixed with diatomaceous earth until paste formation, filtered on diatomaceous earth and rewashed with ethyl acetate. The filtrate is concentrated by evaporation, and the crude product is chromatographed on silica gel with hexane/0-10% ethyl acetate. 337 mg of 5-[3-methoxy-2-(2-methoxycarbonylethyl)-6-pyridyl]-5-oxopentanoic acid methyl ester of melting point 64°-66° C. is obtained.

후처리

  1. additionmixed with diatomaceous earth until paste formation
  2. filtrationfiltered on diatomaceous earth
  3. concentrationThe filtrate is concentrated by evaporation
  4. customthe crude product is chromatographed on silica gel with hexane/0-10% ethyl acetate

출처 및 근거

ORD 기록
ord-08fb447da1ad4f388ff867a35f5f01ae
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05624943

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