Sodium borohydride → HCID 20344139, compound

HRID 2049663Notes

Reaction equation

HRID 2049663 reaction equation
[BH4-].[Na+].Cl.[CH3:4][O:5][C:6]1[CH:7]=[C:8]([C:12](=[O:19])[CH2:13][CH:14]2[CH2:18][CH2:17][CH2:16][NH:15]2)[CH:9]=[CH:10][CH:11]=1>CO.O>[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH:12]([OH:19])[CH2:13][CH:14]2[CH2:18][CH2:17][CH2:16][NH:15]2)[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 20344162HCID 20344162, compound

Product 1

HCID 20344139HCID 20344139, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

4.8 g of sodium borohydride are added portionwise with stirring to a solution of 6.5 g of 1-(3-methoxyphenyl)-2-(2-pyrrolidinyl)-ethanone hydrochloride in 25 ml of methanol and 5 ml of water. After 1 hour the bulk of the methanol is distilled off under a vacuum. The residue is taken up with 20 ml of water and 10 ml of 6 N sodium hydroxide solution. The mixture is extracted 5 times with, in each case, 20 ml of diethylether. The organic phases are collected, dried over sodium sulphate and concentrated to an oil which is distilled. 4.5 g of the title compound are obtained as mixture of diastereoisomers of b.p. 136° at 0.005 mm Hg.

Workup

  1. distillationAfter 1 hour the bulk of the methanol is distilled off under a vacuum
  2. extractionThe mixture is extracted 5 times with, in each case, 20 ml of diethylether
  3. customThe organic phases are collected
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated to an oil which
  6. distillationis distilled

Sources & evidence

ORD record
ord-75e3fda0aa234e69a856795cda88d449
Source dataset
uspto-grants-1980_04
Patent number
US04198424

Reaction notes

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