Sodium borohydride → HCID 10735747, compound

HRID 1069629Notes

Reaction equation

HRID 1069629 reaction equation
[CH2:1]([C:3]1[N:4]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:5]2[C:10]([C:11]=1[C:12](=[O:16])[C:13]([NH2:15])=[O:14])=[C:9]([O:17][CH3:18])[CH:8]=[CH:7][CH:6]=2)[CH3:2].[BH4-].[Na+]>C(O)C>[CH2:1]([C:3]1[N:4]([CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:5]2[C:10]([C:11]=1[CH:12]([OH:16])[C:13]([NH2:15])=[O:14])=[C:9]([O:17][CH3:18])[CH:8]=[CH:7][CH:6]=2)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 10830680HCID 10830680, compound

Product 1

HCID 10735747HCID 10735747, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1 g (3 mmol) of 2-ethyl-4-methoxy-alpha-oxo-1-(phenylmethyl)-1H-indole-3-acetamide and 142 mg (3.75 mmol) of sodium borohydride and 100 mL of ethanol was stirred for 20 hours, and evaporated at reduced pressure. The residue was taken up in ethyl acetate and water, the ethyl acetate separated and washed with brine and dried (MgSO4). The solution was concentrated at reduced pressure and the residue stirred with ether. The insoluble material was filtered to give 893 mg (88%) of 2-ethyl-4-methoxy-alpha-hydroxy-1-(phenylmethyl)-1H-indole-3-acetamide, mp, 160-162° C.

Workup

  1. customevaporated at reduced pressure
  2. customwater, the ethyl acetate separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationThe solution was concentrated at reduced pressure
  6. stirringthe residue stirred with ether
  7. filtrationThe insoluble material was filtered

Sources & evidence

ORD record
ord-ab4c4e407f9f4729a436ec68d3a8b271
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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