Sodium borohydride → HCID 13362029, compound

HRID 569254Notes

Reaction equation

HRID 569254 reaction equation
[BH4-].[Na+].[CH2:3]([N:10]1[C:14](=[O:15])[CH2:13][CH:12]([C:16](OC)=[O:17])[CH:11]1[C:20]1[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:27])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO>[CH2:3]([N:10]1[C:14](=[O:15])[CH2:13][CH:12]([CH2:16][OH:17])[CH:11]1[C:20]1[C:21]([Cl:27])=[CH:22][CH:23]=[CH:24][C:25]=1[Cl:26])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 13362028HCID 13362028, compound

Product 1

HCID 13362029HCID 13362029, compoundYield 129.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 580 ml of methanol was added 72 g. of sodium borohydride at 0°-5°. After the addition, 40 g of methyl 1-benzyl-2-(2,6-dichlorophenyl)-5-oxopyrrolidin-3-carboxylate was then added in portions at 0°-5°. The reaction was stirred at 10°-15° and then left standing overnight at ambient temperature. After concentrating the mixture in vacuo to a solid, the crude product was suspended in water at 50° and stirred for 30 minutes. The resulting solid was collected by filtration and dissolved in chloroform. Drying (Na2SO4), filtration, and concentration in vacuo provided 48 g of off-white crystals, m.p. 122°-126°.

Workup

  1. customat 0°-5°
  2. additionwas then added in portions at 0°-5°
  3. waitleft
  4. concentrationAfter concentrating the mixture in vacuo to a solid
  5. customwas suspended in water at 50°
  6. stirringstirred for 30 minutes
  7. filtrationThe resulting solid was collected by filtration
  8. dissolutiondissolved in chloroform
  9. customDrying
  10. filtration(Na2SO4), filtration, and concentration in vacuo

Sources & evidence

ORD record
ord-07e1cb9395d44fad84c816fb4ea8b185
Source dataset
uspto-grants-1988_03
Patent number
US04731457

Reaction notes

Loading…