Dichloromethane → HCID 59363373, 화합물

HRID 905964노트

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HRID 905964 반응식
[C:1]([O:5]C(=O)NC1CCCN(CC(F)(F)F)C1)(C)(C)C.CC[N:22]([CH:26]([CH3:28])C)[CH:23]([CH3:25])C.[C:29](Cl)(=[O:31])[CH3:30].[CH2:33](Cl)Cl>>[C:29]([N:22]1[CH2:23][CH2:25][C:1](=[O:5])[CH:28]([CH3:33])[CH2:26]1)(=[O:31])[CH3:30]

참가 물질

5

반응물 4

HCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 67386443Racemic [1-(2,2,2-trifluoro-ethyl)-piperidin-3-yl]-carbamic acid tert-butyl ester

생성물 1

HCID 59363373HCID 59363373, 화합물수율 94%

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온도
25 °C

실험 절차

To a suspension of the product of step 1 in DCM at 0° C., DIPEA (4 eqv) was added slowly and stirred for 30 minutes at 25° C. The reaction mixture was cooled again to 0° C. and acetyl chloride (1.1 eqv) was added slowly. The resulting mixture was stirred at 25° C. for 16 hrs before being quenched by addition of saturated aqueous NaHCO3. The aqueous layer was back extracted three times with DCM. The combined organics were washed with H2O, dried (Na2SO4), filtered and evaporated. The residue was purified by SiO2 flash chromatography to give racemic 1-acetyl-3-methyl-piperidin-4-one (94% over two steps).

후처리

  1. temperatureThe reaction mixture was cooled again to 0° C.
  2. stirringThe resulting mixture was stirred at 25° C. for 16 hrs
  3. custombefore being quenched by addition of saturated aqueous NaHCO3
  4. extractionThe aqueous layer was back extracted three times with DCM
  5. washThe combined organics were washed with H2O
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by SiO2 flash chromatography

출처 및 근거

ORD 기록
ord-fcecddb673734e6fbecb6ae7b1435cca
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012974B2

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