Sodium borohydride → tert-Butyl 6-(hydroxymethyl)-1H-indole-1-carboxylate

HRID 551500Notes

Reaction equation

HRID 551500 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH:17]=[O:18])[CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][OH:18])[CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 14616867Tert-butyl 6-formyl-1H-indole-1-carboxylate

Product 1

HCID 23560816tert-Butyl 6-(hydroxymethyl)-1H-indole-1-carboxylateYield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 6-formyl-indole-1-carboxylic acid tert-butyl ester (1.2 g) in methanol (5 mL) in an ice bath was added sodium borohydride (0.27 mg) portion wise. The reaction was allowed to warm to room temperature over 1.5 hr. The reaction diluted with ethyl acetate (200 mL) washed with water (200 mL), brine (100 mL), dried over sodium sulfate, concentrated, adsorbed onto silica gel and purified by flash chromatography with a gradient from 5-40% ethyl acetate in hexanes to yield 6-hydroxymethyl-indole-1-carboxylic acid tert-butyl ester as a clear viscous oil (0.91 g, 78%) LC-MS (ES) calculated for C14H17NO3, 247.1; found m/z 246 [M−H]−.

Workup

  1. washwashed with water (200 mL), brine (100 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. custompurified by flash chromatography with a gradient from 5-40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-9a2b0b784e274660a39d5f4ea3df2cd7
Source dataset
uspto-grants-2011_05
Patent number
US07947728B1

Reaction notes

Loading…