Acetone → 1-Hydroxy-2,2,5,5-tetramethylpyrrolidine-3-carboxamide

HRID 359580Notes

Reaction equation

HRID 359580 reaction equation
[CH3:1][C:2]1([CH3:12])[CH:6]([C:7]([NH2:9])=[O:8])[CH2:5][C:4]([CH3:11])([CH3:10])[NH:3]1.CC(C)=[O:15]>>[OH:15][N:3]1[C:4]([CH3:11])([CH3:10])[CH2:5][CH:6]([C:7]([NH2:9])=[O:8])[C:2]1([CH3:12])[CH3:1]

Participants

3

Reactant 2

HCID 180Acetone2×HCID 697083-Pyrrolidinecarboxamide, 2,2,5,5-tetramethyl-

Product 1

HCID 922111-Hydroxy-2,2,5,5-tetramethylpyrrolidine-3-carboxamide

Procedure

A solution of 0.066 M DMD in acetone (9 ml, 0.59 mmol) was added to a cold stirred solution of 2,2,5,5-tetramethyl-pyrroline-3-carboxamide (Frinton, Vineland NJ, 100 mg, 0.59 mmol) in acetone (5 ml). The mixture was stirred for two hours. Evaporation of the solvent on a rotary evaporator gave a colorless crystalline solid which was dried in vacuo for 6 hours. Sublimation of the solid at 10-3 torr gave a white solid, mp 65-171.

Workup

  1. customEvaporation of the solvent
  2. customon a rotary evaporator
  3. customgave a colorless crystalline solid which
  4. customwas dried in vacuo for 6 hours
  5. customSublimation of the solid at 10-3 torr gave a white solid, mp 65-171

Sources & evidence

ORD record
ord-83446c8f068042eb9071282f4fb53fa3
Source dataset
uspto-grants-1991_03
Patent number
US05001233

Reaction notes

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