3-Methylbutanal → HCID 131733452, compound

HRID 2278355Notes

Reaction equation

HRID 2278355 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]([NH2:17])[CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[S:5][CH:6]=1.[CH3:18][CH:19]([CH3:23])[CH2:20][CH:21]=O.[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]([NH:17][CH2:21][CH2:20][CH:19]([CH3:23])[CH3:18])[CH2:8][O:9][Si:10]([C:13]([CH3:14])([CH3:16])[CH3:15])([CH3:12])[CH3:11])[S:5][CH:6]=1

Participants

5

Reactant 3

HCID 115523-MethylbutanalHCID 4311764Sodium borohydrideHCID 89525790HCID 89525790, compound

Product 1

HCID 131733452HCID 131733452, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(4-bromothiophen-2-yl)-2-{[tert-butyl(dimethyl)silyl]oxy}ethanamine (216 mg, 0.642 mmol) was dissolved in 1.5 mL MeOH. Molecular sieves (3 Å) and 3-methylbutanal (79 μL, 0.739 mmol) were then added. The resulting mixture was stirred at room temperature overnight. Sodium borohydride (36.4 mg, 0.963 mmol) was added and the mixture was stirred for 1 hour, and then quenched with aqueous sodium hydrogen carbonate. DCM was added and the phases separated. The solvent was removed under reduced pressure. The resulting solid was used without further purification.

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. customquenched with aqueous sodium hydrogen carbonate
  3. additionDCM was added
  4. customthe phases separated
  5. customThe solvent was removed under reduced pressure
  6. customThe resulting solid was used without further purification

Sources & evidence

ORD record
ord-471869fab8714a939edcc8cdcf7ed0d6
Source dataset
uspto-grants-2015_09
Patent number
US09133157B2

Reaction notes

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