Sodium borohydride → HCID 12550011, compound

HRID 423873Notes

Reaction equation

HRID 423873 reaction equation
[BH4-].[Na+].[CH3:3][CH:4]([CH3:16])[C:5](=[O:15])[CH2:6][CH2:7][NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CO>[CH3:3][CH:4]([CH3:16])[CH:5]([OH:15])[CH2:6][CH2:7][NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 574702544-Methyl-1-(phenylamino)-pentan-3-one

Product 1

HCID 12550011HCID 12550011, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

At −10° C., NaBH4 (56.7 g, 1.5 mol) was gradually added to a mixture of the crude 4-methyl-1-(phenylamino)-pentan-3-one (about 80 g) in MeOH (500 mL). After addition, the reaction mixture was allowed to warm to room temperature and stirred for 20 min. The solvent was removed and the residue was repartitioned between water and CH2Cl2. The organic phase was separated, washed with brine, dried over Na2SO4, filtered and concentrated. The resulting gum was triturated with ether to give 4-methyl-1-(phenylamino)-pentan-3-ol as a white solid (22 g, 23%).

Workup

  1. additionAfter addition
  2. customThe solvent was removed
  3. customThe organic phase was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting gum was triturated with ether

Sources & evidence

ORD record
ord-02c64868605b454cafecde5aa1534be9
Source dataset
uspto-grants-2012_01
Patent number
US08101767B2

Reaction notes

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