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

HRID 55282

反応式

HRID 55282 の反応式
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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8058Hexane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-08fb447da1ad4f388ff867a35f5f01ae
出典データセット
uspto-grants-1997_04
特許番号
US05624943

関連ノート

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