Water → HCID 57907634、化合物

HRID 243701ノート

反応式

HRID 243701 の反応式
P(Cl)(Cl)([Cl:3])=O.[N+:6]1([O-])[CH:11]=[CH:10][CH:9]=[C:8]2[CH2:12][CH2:13][CH:14]([C:15]([O:17][CH3:18])=[O:16])[C:7]=12.O>CN(C=O)C.C(Cl)(Cl)Cl>[Cl:3][C:11]1[N:6]=[C:7]2[CH:14]([C:15]([O:17][CH3:18])=[O:16])[CH2:13][CH2:12][C:8]2=[CH:9][CH:10]=1

参加物

6

反応物 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 57907387HCID 57907387、化合物

生成物 1

HCID 57907634HCID 57907634、化合物収率 62.2%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a cooled (0° C.) solution of 0.21 mL (2.28 mmol) of phosphorous oxychloride in 0.2 mL of anhydrous DMF was added a solution of 1.1 g (5.69 mmol) of methyl 6,7-dihydro-5H-cyclopenta[b]pyridine-7-carboxylate 1-oxide from Step B above in 15 mL chloroform dropwise over 10 min. The resulting solution was allowed to warm to ambient temperature and then refluxed for 4 h. The mixture was cooled and poured into 30 mL of cold water. The aqueous solution was extracted with diethyl ether (3×30 mL) followed by a single extraction with 30 mL of dichloromethane. The combined organic layers were dried over magnesium sulfate, filtered and evaporated in vacuo. The resulting brown residue was purified by silica gel chromatography eluting with 50% ethyl acetate in hexane to afford the title compound as a light brown solid (0.30 g, 25%). LC-MS: m/z (E/S) 212.0 (MH)+.

後処理

  1. temperaturerefluxed for 4 h
  2. temperatureThe mixture was cooled
  3. extractionThe aqueous solution was extracted with diethyl ether (3×30 mL)
  4. extractionfollowed by a single extraction with 30 mL of dichloromethane
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe resulting brown residue was purified by silica gel chromatography
  9. washeluting with 50% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-7d3fd9340ccc4948a90d44feb1844ab0
出典データセット
uspto-grants-2014_02
特許番号
US08653260B2

反応ノート

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