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

HRID 489111노트

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HRID 489111 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-752f0f9d91f947a5a7e11ac961c71da0
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06974831B2

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