Water → HCID 57907634, compound

HRID 1947732Notes

Reaction equation

HRID 1947732 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-3b850183ad604064aa05f8676fa91a7f
Source dataset
uspto-grants-2013_03
Patent number
US08399480B2

Reaction notes

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