Hydrochloric Acid → 3alpha-Pentafluoropropionyloxy-5alpha-pregnan-20-one

HRID 232803

반응식

HRID 232803 반응식
[OH:1][C@@H:2]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[CH2:17][CH2:16][C@@:15]2([CH3:23])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1.C(N(CC)CC)C.[F:31][C:32]([F:40])([C:36]([F:39])([F:38])[F:37])[C:33](Cl)=[O:34].Cl>CN(C)C1C=CN=CC=1.ClCCl.CCOCC>[F:31][C:32]([F:40])([C:36]([F:39])([F:38])[F:37])[C:33]([O:1][C@@H:2]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[CH2:17][CH2:16][C@@:15]2([CH3:23])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1)=[O:34]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 67911Perfluoropropionyl chlorideHCID 92786Allopregnanolone

생성물 1

HCID 867470843alpha-Pentafluoropropionyloxy-5alpha-pregnan-20-one

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

To an ice-cooled, stirred mixture of 3α-hydroxy-5α-pregnan-20-one (260 mg, 318.5 g/m, 0.82 mmol), triethylamine (0.17 mL), and 4-dimethylaminopyridine (DMAP catalytic, 10 mg, 122.17 g/m, 82 umol) dissolved in 17 mL of dry dichloromethane under a nitrogen atmosphere was added pentafluoropropionyl chloride (168 mg, 182.5 g/m 0.92 mmol). The reaction was stirred at 0° C. for 10 hours and then poured into 100 mL of 10% HCl and 200 mL of ether. The organic phase was washed once more with acid, twice with saturated sodium bicarbonate, and then dried over magnesium sulfate. After removal of solvent in vacuo, the crude product was purified by filtration through a bed of silica gel with hexane/ethyl acetate (15:35) elution. The product was isolated from the two earliest fractions (100 mL each) to give (330 mg, 464.5 g/m, 0.71 mmol, 87%).

후처리

  1. stirringThe reaction was stirred at 0° C. for 10 hours
  2. washThe organic phase was washed once more with acid, twice with saturated sodium bicarbonate
  3. dry with materialdried over magnesium sulfate
  4. customAfter removal of solvent in vacuo
  5. filtrationthe crude product was purified by filtration through a bed of silica gel with hexane/ethyl acetate (15:35) elution
  6. customThe product was isolated from the two earliest fractions (100 mL each)
  7. customto give (330 mg, 464.5 g/m, 0.71 mmol, 87%)

출처 및 근거

ORD 기록
ord-486269d742414e15a41fd9f3acc90e6d
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05591733

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