Sodium borohydride → HCID 21399023, compound

HRID 1439264Notes

Reaction equation

HRID 1439264 reaction equation
[BH4-].[Na+].C[O:4][C:5](=O)[C@H:6]([CH2:16][C:17]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[C:19]([O:25][CH3:26])[CH:18]=1)[NH:7][C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O1CCCC1>[C:8]([NH:7][CH:6]([CH2:16][C:17]1[CH:18]=[C:19]([O:25][CH3:26])[CH:20]=[C:21]([O:23][CH3:24])[CH:22]=1)[CH2:5][OH:4])(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22800153HCID 22800153, compound

Product 1

HCID 21399023HCID 21399023, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.2 gm of sodium borohydride were added to a stirred mixture of 34.3 gm of N-benzoyl-3-(3',5'-dimethoxy-phenyl)alanine methyl ester and 350 ml of tetrahydrofuran at room temperature, the resulting mixture was stirred for 30 minutes more at room temperature, and then it was refluxed for five hours. After cooling of the reaction mixture, the solvent was distilled off in vacuo, the residue was suspended in water, and the suspension was acidified with acetic acid. The crystalline precipitate formed thereby was collected by suction filtration, washed with water, dried and recrystallized from toluene, yielding 2-benzamido-3-(3',5'-dimethoxy-phenyl)-1-propanol having a melting point of 117°-118° C.

Workup

  1. temperatureit was refluxed for five hours
  2. temperatureAfter cooling of the reaction mixture
  3. distillationthe solvent was distilled off in vacuo
  4. customThe crystalline precipitate formed
  5. filtrationthereby was collected by suction filtration
  6. washwashed with water
  7. customdried
  8. customrecrystallized from toluene

Sources & evidence

ORD record
ord-5912350648034faaba4dcf10bb66a2ab
Source dataset
uspto-grants-1977_11
Patent number
US04058642

Reaction notes

Loading…