Methanol → HCID 13362007, compound

HRID 980930Notes

Reaction equation

HRID 980930 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[CH2:11][CH:10]([C:14](OC)=[O:15])[CH:9]1[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[BH4-].[Na+]>O>[CH2:1]([N:8]1[CH:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=2)[CH:10]([CH2:14][OH:15])[CH2:11][C:12]1=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 13362006HCID 13362006, compound

Product 1

HCID 13362007HCID 13362007, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To 42.1 gm. of methyl 1-benzyl-2-(3-methoxyphenyl)-5-oxopyrrolidin-3-carboxylate in 436 ml. of absolute methanol was slowly added at -10° to -5°, 37.9 gm. of sodium borohydride. The reaction mixture was left in the ice bath until it came to ambient temperature. Concentration in vacuo provided a white gum which was suspended in water and heated to 50° C. The gum was extracted with chloroform, dried (Na2SO4), filtered, and concentrated in vacuo to yield 22.8 gm. of yellow oil.

Workup

  1. customcame to ambient temperature
  2. concentrationConcentration in vacuo
  3. customprovided a white gum which
  4. extractionThe gum was extracted with chloroform
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto yield 22.8 gm

Sources & evidence

ORD record
ord-96f51835377849d0bb8f40172ac48d10
Source dataset
uspto-grants-1987_01
Patent number
US04639529

Reaction notes

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