Hydrochloric Acid → HCID 22903658, compound

HRID 1489164Notes

Reaction equation

HRID 1489164 reaction equation
[CH2:1]([N:8]1[C:12](=O)[CH2:11][C:10]([C:17](=O)[N:18]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14](O)=[O:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].S(=O)(=O)(O)O.Cl>O1CCCC1>[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([CH2:17][N:18]([CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)([CH2:14][OH:15])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 4311764Sodium borohydrideHCID 22903696HCID 22903696, compound

Product 1

HCID 22903658HCID 22903658, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1-Benzyl-3-(N,N-dibenzylcarbamoyl)-5-oxopyrrolidine-3-carboxylic acid (124 g) was dissolved in tetrahydrofuran (1.1 l) and sodium borohydride (79.7 g) was added over 15 minutes under ice-cooling. A solution of sulfuric acid (56 ml) in tetrahydrofuran (560 ml) was added over 1 hour under ice-cooling, and the mixture was refluxed for 3 hours. 3N Hydrochloric acid (500 ml) was added under ice-cooling and the mixture was refluxed for 2.5 hours. After concentration, water (1 l) was added and the resulting mixture was made alkaline with an aqueous solution of sodium hydroxide. The resulting mixture was extracted with ethyl acetate and washed with saturated brine. After drying, the organic layer was concentrated and purified by silica gel column chromatography to give 90 g of the object compound as white crystals, melting point 65°-67° C.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. temperaturethe mixture was refluxed for 3 hours
  4. temperaturecooling
  5. temperaturethe mixture was refluxed for 2.5 hours
  6. concentrationAfter concentration, water (1 l)
  7. additionwas added
  8. extractionThe resulting mixture was extracted with ethyl acetate
  9. washwashed with saturated brine
  10. customAfter drying
  11. concentrationthe organic layer was concentrated
  12. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-c67045a845f9451faf5c6ab744a5b6e0
Source dataset
uspto-grants-1997_10
Patent number
US05677316

Reaction notes

Loading…