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

HRID 489111Notes

Reaction equation

HRID 489111 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-752f0f9d91f947a5a7e11ac961c71da0
Source dataset
uspto-grants-2005_12
Patent number
US06974831B2

Reaction notes

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