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Sodium Carbonate → (7S,8aS)-7-(4-Fluorophenoxy)methyl-2-(6-chloropyrazin-2-yl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine

HRID 861356
ノート
印刷プレビュー

反応式

HRID 861356 の反応式
[F:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][CH2:7][CH:8]2[CH2:16][N:11]3[CH2:12][CH2:13][NH:14][CH2:15][CH:10]3[CH2:9]2)=[CH:4][CH:3]=1.[Cl:19][C:20]1[CH:25]=[N:24][CH:23]=[C:22](Cl)[N:21]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)CC(C)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C@@H:8]2[CH2:16][N:11]3[CH2:12][CH2:13][N:14]([C:22]4[CH:23]=[N:24][CH:25]=[C:20]([Cl:19])[N:21]=4)[CH2:15][C@@H:10]3[CH2:9]2)=[CH:17][CH:18]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 785042,6-DichloropyrazineHCID 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 86752024(7S,8aS)-7-(4-Fluorophenoxy)methyl-2-(6-chloropyrazin-2-yl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine収率 68%

試薬・触媒・溶媒 1

HCID 31260
Isoamyl Alcohol
溶媒

実験手順

A mixture of 0.500 g (2.00 mmol) of (7SR,8aSR)-7-(4-fluoro-phenoxy)methyl-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine (Preparation 3), 1.49 g (10.0 mmol) of 2,6-dichloropyrazine, and 0.508 g (4.79 mmol) of sodium carbonate in 50 mL of isoamyl alcohol was heated to reflux for 16 h. The reaction was cooled to ambient temperature, the solvent removed in vacuo, the residue taken up in ethyl acetate and water, the pH was adjusted to 11 with sodium carbonate and the layers were separated. The aqueous phase was extracted with ethyl acetate, and the combined organic layers were dried (magnesium sulfate), filtered and evaporated. Purification by flash silica gel chromatography with 90:10 ethyl acetate:hexane gave 0.491 g (68%) of the title compound. mp (.HCl) 209°-212° C. HRMS calcd for C18H21ClFN4O (MH+): 363.1388, found: 363.1384.

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 16 h
  3. customthe solvent removed in vacuo
  4. customthe layers were separated
  5. extractionThe aqueous phase was extracted with ethyl acetate
  6. dry with materialthe combined organic layers were dried (magnesium sulfate)
  7. filtrationfiltered
  8. customevaporated
  9. customPurification by flash silica gel chromatography with 90:10 ethyl acetate

出典と根拠

ORDレコード
ord-4ed936f7cfd04f7dac10c7a2477c6fd0
出典データセット
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05714487

反応ノート

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