Water → HCID 57907634, 화합물

HRID 887132노트

반응식

HRID 887132 반응식
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

참가 물질

6

반응물 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 57907387HCID 57907387, 화합물

생성물 1

HCID 57907634HCID 57907634, 화합물수율 62.2%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6228Dimethylformamide용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-fd263dc762f34e10b0e472f0e681212d
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247415B2

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