Sodium borohydride → HCID 10566917, compound

HRID 1069636Notes

Reaction equation

HRID 1069636 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[C:5]([C:19](=[O:23])[C:20]([NH2:22])=[O:21])=[CH:6][N:7]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[BH4-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[C:5]([CH:19]([OH:23])[C:20]([NH2:22])=[O:21])=[CH:6][N:7]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 10804720HCID 10804720, compound

Product 1

HCID 10566917HCID 10566917, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.4 g (4.5 mmol) of 4-methoxy-alpha-oxo-1-(phenylmethyl)-1H-indole-3-acetamide and 213 mg (5.6 mmol) of sodium borohydride and 50 mL of ethanol was stirred for 20 hours, 213 mg (5.6 mmol), of sodium borohydride added and stirred an additional 20 hours and the mixture filtered and evaporated at reduced pressure. The residue was stirred with ethyl acetate and water and the insoluble material was filtered to give 600 mg (43%) of 4-methoxy-alpha-hydroxy-1-(phenylmethyl)-1H-indole-3-acetamide, mp, 179-182° C.

Workup

  1. stirringstirred an additional 20 hours
  2. filtrationthe mixture filtered
  3. customevaporated at reduced pressure
  4. stirringThe residue was stirred with ethyl acetate and water
  5. filtrationthe insoluble material was filtered

Sources & evidence

ORD record
ord-c87e275df7ab4fa2b475b3fa72fdbe22
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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