Citric Acid → 1-Benzyl-2-(1-hydroxyethyl)-4-methoxy-6,7,8,9-tetrahydro-1h-benz[g]indole

HRID 489111ノート

反応式

HRID 489111 の反応式
[C:1]([C:4]1[N:5]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:6]2[C:11]([CH:12]=1)=[C:10]([O:13][CH3:14])[CH:9]=[C:8]1[CH2:15][CH2:16][CH2:17][CH2:18][C:7]=21)(=[O:3])[CH3:2].[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C>[CH2:19]([N:5]1[C:6]2[C:11](=[C:10]([O:13][CH3:14])[CH:9]=[C:8]3[CH2:15][CH2:16][CH2:17][CH2:18][C:7]3=2)[CH:12]=[C:4]1[CH:1]([OH:3])[CH3:2])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

参加物

5

反応物 3

HCID 311Citric AcidHCID 4311764Sodium borohydrideHCID 114730712-Acetyl-1-benzyl-4-methoxy-6,7,8,9-tetrahydro-1h-benz[g]indole

生成物 1

HCID 114731251-Benzyl-2-(1-hydroxyethyl)-4-methoxy-6,7,8,9-tetrahydro-1h-benz[g]indole

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 2-acetyl-1-benzyl-4-methoxy-6,7,8,9-tetrahydro-1H-benz[g]indole (4.68 g, 14.0 mmol) in ethanol (50 mL) was added sodium borohydride (537 mg, 14.0 mmol). After stirring for 2 h, 10% aqueous citric acid (10 mL) was added and the mixture concentrated in vacuo. The residue was dissolved in ethyl acetate, washed once with water, and once with saturated sodium bicarbonate solution. The organic layer was dried (magnesium sulfate), filtered and concentrated in vacuo to provide the title compound in quantitative yield. 1H NMR (CDCl3) δ 7.20 (m, 3H), 6.79 (d, J=7.0 Hz, 2H), 6.65 (s, 1H), 6.24 (s, 1H), 5.76 (s, 2H), 4.75 (quintet, J=6.6 Hz, 1H), 3.91 (s, 3H), 2.97 (m, 1H), 2.84 (m, 3H), 1.70 (m, 4H), 1.60 (d, J=6.6 Hz, 3H); MS ES+ m/e 336 (p+1).

後処理

  1. concentrationthe mixture concentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed once with water
  4. dry with materialThe organic layer was dried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-752f0f9d91f947a5a7e11ac961c71da0
出典データセット
uspto-grants-2005_12
特許番号
US06974831B2

反応ノート

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