Sodium borohydride → Methyl 4-[5-(2-hydroxyethyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate

HRID 2248777Notes

Reaction equation

HRID 2248777 reaction equation
[BH4-].[Na+].[CH:3]([CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][CH2:16][CH3:17])[CH:10]=[C:9]2[CH2:18][C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][C:20]=1[O:29][CH3:30])=[O:4]>CO>[OH:4][CH2:3][CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][CH2:16][CH3:17])[CH:10]=[C:9]2[CH2:18][C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][C:20]=1[O:29][CH3:30]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 19994986Methyl 4-[5-(formylmethyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate

Product 1

HCID 19994996Methyl 4-[5-(2-hydroxyethyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoateYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.027 g) was added to a stirred solution of methyl 4-[5-(formylmethyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate (0.54 g) in methanol (15 ml) under a nitrogen atmosphere. After 30 min, the solvent was evaporated. The residue was dissolved in ethyl acetate, washed with water (twice), brine, and then dried (MgSO4) and evaporated. The product was purified by flash chromatography, eluting with 7:3 hexane:ethyl acetate, to give methyl 4-[5-(2-hydroxyethyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate (0.35 g, 65%) as an oil: partial NMR (300 MHz, DMSO-d6): 0.80(t, 3H, CH3), 1.70(m, 2H, CH2), 2.74(t, 2H, CH2), 3.56(t, 2H, CH2), 3.83(s, 3H, OCH3), 3.91(s, 3H, OCH3), 4.03(m, 4H, NCH2, ArCH2Ar').

Workup

  1. customthe solvent was evaporated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with water (twice), brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe product was purified by flash chromatography
  7. washeluting with 7:3 hexane

Sources & evidence

ORD record
ord-8340c86303114426909084b842b00ec9
Source dataset
uspto-grants-1991_08
Patent number
US05041460

Reaction notes

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