Sodium borohydride → HCID 58200033, compound

HRID 1907263Notes

Reaction equation

HRID 1907263 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][CH2:9][CH2:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])=[O:12])[CH:5]=[CH:6][CH:7]=1.[BH4-].[Na+]>C1COCC1.CO>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][CH2:9][CH2:10][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[OH:12])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58200043HCID 58200043, compound

Product 1

HCID 58200033HCID 58200033, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of 3-(3-bromophenylamino)-1-(2-chlorophenyl)propan-1-one (50 mg, 0.148 mmol) in 4:1 THF/methanol (5 mL) was cooled to 0° C. NaBH4 (11 mg, 2 equiv) was added. After 10 min, the mixture was warmed up to rt slowly and stirred for 2 h. The mixture was concentrated, diluted with EtOAc (7 mL), washed with 1% aq HCl (1 mL), and dried over Na2SO4. Filtration and concentration afforded crude 3-(3-bromophenylamino)-1-(2-chlorophenyl)propan-1-ol which was used without further purification. LC-MS (3 min) tR=1.93 min, m/z=342,343(M+1).

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with EtOAc (7 mL)
  3. washwashed with 1% aq HCl (1 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-2ab356c6c25348488dded2d81ff4981e
Source dataset
uspto-grants-2013_12
Patent number
US08598160B2

Reaction notes

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