o-Methylvalerolactim → 3-(3,4-Difluorophenyl)-5,6,7,8-tetrahydroimidazo-[1,5-a]pyridine-1-carboxylic acid

HRID 75116

반응식

HRID 75116 반응식
CO[C:3]1[CH2:4][CH2:5][CH2:6][CH2:7][N:8]=1.[F:9][C:10]1[CH:11]=[C:12]([C:17]2[O:18][C:19](=[O:22])[CH2:20][N:21]=2)[CH:13]=[CH:14][C:15]=1[F:16].O.[OH-].[Li+]>C1COCC1.O>[F:9][C:10]1[CH:11]=[C:12]([C:17]2[N:8]3[CH2:7][CH2:6][CH2:5][CH2:4][C:3]3=[C:20]([C:19]([OH:22])=[O:18])[N:21]=2)[CH:13]=[CH:14][C:15]=1[F:16]

참가 물질

6

반응물 3

HCID 138567o-MethylvalerolactimHCID 168937Lithium hydroxide, monohydrateHCID 580541722-(3,4-difluorophenyl)oxazol-5(4H)-one

생성물 1

HCID 580541853-(3,4-Difluorophenyl)-5,6,7,8-tetrahydroimidazo-[1,5-a]pyridine-1-carboxylic acid수율 71%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
90 °C

실험 절차

6-methoxy-2,3,4,5-tetrahydropyridine (0.431 g, 3.80 mmol) was dissolved in THF (5 mL) in a 40 mL screw-cap vial and 2-(3,4-difluorophenyl)oxazol-5(4H)-one (0.75 g, 3.80 mmol) in THF (5 mL) was added, producing an orange solution. The vial was capped and heated to 90° C. for 3 hours. THF was removed under reduced pressure and the residue was dissolved in MeOH (10 ml) and lithium hydroxide monohydrate (0.479 g, 11.41 mmol) in water (1 mL) was added. The reaction was heated to 90° C. for 3 hours. MeOH was removed by evaporation under reduced pressure. The remaining aqueous solution was diluted with water (5 mL) and acidified to pH 2 with 5M HCl. The solution was extracted with EtOAc (3×5 mL). The combined organic extracts were dried over anhydrous sodium sulfate, filtered and evaporated to yield the desired product as a brown oil (742 mg, 71%) that was used without further purification. LCMS (+ESI) m/z: 279.3 [M+H]+.

후처리

  1. customscrew-cap vial
  2. customproducing an orange solution
  3. customThe vial was capped
  4. customTHF was removed under reduced pressure
  5. dissolutionthe residue was dissolved in MeOH (10 ml)
  6. temperatureThe reaction was heated to 90° C. for 3 hours
  7. customMeOH was removed by evaporation under reduced pressure
  8. additionThe remaining aqueous solution was diluted with water (5 mL)
  9. extractionThe solution was extracted with EtOAc (3×5 mL)
  10. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. customevaporated

출처 및 근거

ORD 기록
ord-6dfdf4e4b2b14b39b3030a94bfc4e3bf
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835422B2

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