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

反応式

HRID 861340 の反応式
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

参加物

5

反応物 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

生成物 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]pyrazine収率 2%

試薬・触媒・溶媒 1

HCID 31260Isoamyl Alcohol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e30d90d564d642e5a4156f87da53c4e3
出典データセット
uspto-grants-1998_02
特許番号
US05714487

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