Water → HCID 57907634, compound

HRID 243701Notes

Reaction equation

HRID 243701 reaction equation
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

Participants

6

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 57907387HCID 57907387, compound

Product 1

HCID 57907634HCID 57907634, compoundYield 62.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-7d3fd9340ccc4948a90d44feb1844ab0
Source dataset
uspto-grants-2014_02
Patent number
US08653260B2

Reaction notes

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