Butanal → HCID 15523811, compound

HRID 322224Notes

Reaction equation

HRID 322224 reaction equation
[NH2:1][CH2:2][C@H:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([CH3:23])([CH3:22])[C:15]([N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[O:16])[CH:12]=2)[NH:7][C:6]=1[C:24]1[CH:29]=[C:28]([CH3:30])[CH:27]=[C:26]([CH3:31])[CH:25]=1)[CH3:4].S([O-])([O-])(=O)=O.[Mg+2].[CH:38](=O)[CH2:39][CH2:40][CH3:41].[BH4-].[Na+]>C(Cl)(Cl)Cl.CO>[CH2:38]([NH:1][CH2:2][C@H:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([CH3:23])([CH3:22])[C:15]([N:17]([CH2:18][CH3:19])[CH2:20][CH3:21])=[O:16])[CH:12]=2)[NH:7][C:6]=1[C:24]1[CH:29]=[C:28]([CH3:30])[CH:27]=[C:26]([CH3:31])[CH:25]=1)[CH3:4])[CH2:39][CH2:40][CH3:41]

Participants

7

Reactant 4

HCID 261ButanalHCID 24083Sulfuric acid magnesium salt (1:1)HCID 4311764Sodium borohydrideHCID 15523810HCID 15523810, compound

Product 1

HCID 15523811HCID 15523811, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of (S)-2-[3-(2-amino-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-N,N-diethylisobutyramide in dry chloroform at 0° C. is added magnesium sulfate followed by butyraldehyde and the mixture stirred at low temperature. After 30 minutes, a solution of sodium borohydride in methanol is added and the reaction allowed to proceed at 0° C. After completion, the reaction is quenched by the addition of saturated sodium bicarbonate and the mixture extracted with ethyl acetate. The organic portion is washed with saturated aqueous sodium bicarbonate and then dried over sodium sulfate. Purification of the concentrate by flash chromatography on silica gel gives the title compound.

Workup

  1. customto proceed at 0° C
  2. customAfter completion, the reaction is quenched by the addition of saturated sodium bicarbonate
  3. extractionthe mixture extracted with ethyl acetate
  4. washThe organic portion is washed with saturated aqueous sodium bicarbonate
  5. dry with materialdried over sodium sulfate
  6. customPurification of the
  7. concentrationconcentrate by flash chromatography on silica gel

Sources & evidence

ORD record
ord-dcccf00913314fc586ef268d6a44a40a
Source dataset
uspto-grants-2001_04
Patent number
US06211224B1

Reaction notes

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