Sodium Carbonate → (7RS,8aSR)-7-(4-Fluorophenoxy)methyl-2-(5-chloropyridin-2-yl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine

HRID 861340

반응식

HRID 861340 반응식
Cl[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[F:15][C:16]1[CH:32]=[CH:31][C:19]([O:20][CH2:21][CH:22]2[CH2:30][N:25]3[CH2:26][CH2:27][NH:28][CH2:29][CH:24]3[CH2:23]2)=[CH:18][CH:17]=1>C(O)CC(C)C>[F:15][C:16]1[CH:17]=[CH:18][C:19]([O:20][CH2:21][CH:22]2[CH2:30][N:25]3[CH2:26][CH2:27][N:28]([C:2]4[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=4)[CH2:29][CH:24]3[CH2:23]2)=[CH:31][CH:32]=1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 276852,5-DichloropyridineHCID 20682345(7RS,8aSR)-7-(4-fluorophenoxy)methyl-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine

생성물 1

HCID 9841887(7RS,8aSR)-7-(4-Fluorophenoxy)methyl-2-(5-chloropyridin-2-yl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine수율 2%

시약·촉매·용매 1

HCID 31260Isoamyl Alcohol용매

실험 절차

A mixture of 3.8 g (26 mmol) of 2,5-dichloropyridine, 1.3 g (12 mmol) of sodium carbonate, 1.3 g (5.2 mmol) of (7RS,8aSR)-7-(4-fluorophenoxy)methyl-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine (Preparation 2), and 20 mL of isoamyl alcohol was heated at reflux for 18 h. The solvent was evaporated, the residue taken up in water and ethyl acetate, and the pH adjusted to 11 with sodium carbonate. The layers were separated and the organic phase was dried (magnesium sulfate), filtered, and evaporated. Purification by medium pressure silica gel chromatography with ethyl acetate gave 35 mg (2%) of the title compound. mp (.HCl) 202°-206° C. HRMS calcd for C19H21 ClFN3O (MH+): 362.1435, found: 362.1451.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. customThe solvent was evaporated
  4. customThe layers were separated
  5. dry with materialthe organic phase was dried (magnesium sulfate)
  6. filtrationfiltered
  7. customevaporated
  8. customPurification by medium pressure silica gel chromatography with ethyl acetate

출처 및 근거

ORD 기록
ord-e30d90d564d642e5a4156f87da53c4e3
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05714487

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