tert-butyl 3-formyl-1H-indole-1-carboxylate → tert-Butyl 3-(hydroxymethyl)-1H-indole-1-carboxylate

HRID 742550Notes

Reaction equation

HRID 742550 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:17]=[O:18])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)C>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][OH:18])=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2764519tert-butyl 3-formyl-1H-indole-1-carboxylateHCID 4311764Sodium borohydride

Product 1

HCID 11075767tert-Butyl 3-(hydroxymethyl)-1H-indole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 100mL two-necked round-bottom flask equipped with a thermometer 1-(tert-butyloxycarbonyl)-3-formylindole (13.7 g, 60 mmol) was suspended in ethanol (36 mL). Sodium borohydride (4.40 g, 115 mmol) was added in four portions, during which the temperature did not rise about 20° C., and the mixture was stirred for 6 hours. Then the solvent was evaporated in vacuo. The residual oil was shaken with 1.0N sodium hydroxide (150 mL), and the alkaline solution was extracted with ether (3×180 mL), dried with MgSO4, filtered and evaporated to give a colorless oil which solidified on refrigeration (3.95 g, ca. 100%).

Workup

  1. customdid not rise about 20° C.
  2. customThen the solvent was evaporated in vacuo
  3. stirringThe residual oil was shaken with 1.0N sodium hydroxide (150 mL)
  4. extractionthe alkaline solution was extracted with ether (3×180 mL)
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customto give a colorless oil which

Sources & evidence

ORD record
ord-dfca2fed31e6457aad0fc6eb447d512a
Source dataset
uspto-grants-1996_09
Patent number
US05554753

Reaction notes

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