Sodium borohydride → HCID 44610348、化合物

HRID 1432515ノート

反応式

HRID 1432515 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][N:12]1[CH3:18].[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH:11]1[N:12]([CH3:18])[CH2:13][CH2:14][C:15]([CH3:17])=[CH:16]1

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 44610346HCID 44610346、化合物

生成物 1

HCID 44610348HCID 44610348、化合物収率 73%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a stirred solution of 2-(2,4-dimethoxyphenyl)-1,4-dimethyl-1,2-dihydropyridine (4) (0.48 g, 2.06 mmol) in methanol (5 ml) at room temperature was added sodium borohydride (98 mg, 2.51 mmol), gas evolution commenced immediately, the resulting mixture was stirred for 3 hours. At this time the solvent was evaporated and the residue suspended in water (5 ml) and extracted with ethyl acetate (2×10 ml). The organic extract was then extracted with 2M hydrochloric acid (2×15 ml). The aqueous layer was basified with 2M sodium hydroxide and extracted with ethyl acetate (2×20 ml), the organic extract was dried over anhydrous magnesium sulphate, filtered and evaporated to yield 6-(2,4-dimethoxyphenyl)-1,4-dimethyl-1,2,3,6-tetrahydropyridine (6) (350 mg, 73%) as a yellow oil, 1H NMR CDCl3 δ?1.55 (s, 3H), 1.9 (m, 1H), 2.2 (s, 3H), 2.5 (m, 2H), 2.95 (m, 1H), 3.8 (s, 6H), 4.1 (m, 1H), 5.2 (m, 1H), 6.5 (m, 2H), 7.3 (d, 1H J=4).

後処理

  1. customAt this time the solvent was evaporated
  2. extractionextracted with ethyl acetate (2×10 ml)
  3. extractionThe organic extract
  4. extractionwas then extracted with 2M hydrochloric acid (2×15 ml)
  5. extractionextracted with ethyl acetate (2×20 ml)
  6. extractionthe organic extract
  7. dry with materialwas dried over anhydrous magnesium sulphate
  8. filtrationfiltered
  9. customevaporated

出典と根拠

ORDレコード
ord-4c172235d32247c69787c42062d864d3
出典データセット
uspto-grants-2009_11
特許番号
US07612101B2

反応ノート

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