Ethanol → HCID 12526834, compound

HRID 1908259Notes

Reaction equation

HRID 1908259 reaction equation
[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][C:4]([C:7](=[O:10])[CH2:8]Br)=[CH:3][CH:2]=1.CCO.[N-:20]=[N+]=[N-].[Na+].[BH4-].[Na+]>CO>[NH2:20][CH2:8][CH:7]([C:4]1[CH:5]=[CH:6][C:1]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:2][CH:3]=1)[OH:10]

Participants

6

Reactant 4

HCID 702EthanolHCID 33557Sodium AzideHCID 672821-(1,1'-Biphenyl)-4-yl-2-bromoethanoneHCID 4311764Sodium borohydride4×

Product 1

HCID 12526834HCID 12526834, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution consisting of 1-biphenyl-4-yl-2-bromo-ethanone (412 mg. 1.5 mmol) and EtOH (6 mL) was added NaN3 (107 mg, 1.6 mmol) at rt. The mixture was stirred at rt for 2 h and then cooled to 0° C. NaBH4 (61 mg, 1.6 mmol) was added and the mixture stirred for 45 min. A mixture (black slurry) of CuSO4.5H2O (37 mg)/NaBH4 (28 mg) in MeOH 2 mL) was prepared by adding the NaBH4 to CuSO4.5H2O in MeOH at 0° C. This slurry was poured into the reaction mixture. The reaction vessel was allowed to gradually warm to rt. An additional amount of NaBH4 (28 mg) was added 30 min after the addition of the slurry. The reaction was stirred at rt for 2 h. The mixture was filtered through a pad of celite, adhered to silica gel (7-8 g) and purified (FCC) to give the title compound (256 mg, 80%).

Workup

  1. temperaturecooled to 0° C
  2. stirringthe mixture stirred for 45 min
  3. additionThis slurry was poured into the reaction mixture
  4. temperatureto gradually warm to rt
  5. additionafter the addition of the slurry
  6. stirringThe reaction was stirred at rt for 2 h
  7. filtrationThe mixture was filtered through a pad of celite
  8. custompurified (FCC)

Sources & evidence

ORD record
ord-bfae42555a8b442bb43f0ced9fad772c
Source dataset
uspto-grants-2013_12
Patent number
US08598202B2

Reaction notes

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