Acetone → HCID 68731899, compound

HRID 1876878Notes

Reaction equation

HRID 1876878 reaction equation
[CH3:1][C:2]([C:6]1([OH:21])[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7]1)([CH3:5])[CH:3]=[O:4].CC(C)=[O:24].Cl.O.[Mn]([O-])(=O)(=O)=O.[K+]>>[CH2:14]([O:13][C:11]([N:8]1[CH2:9][CH2:10][C:6]([C:2]([CH3:1])([CH3:5])[C:3]([OH:24])=[O:4])([OH:21])[CH2:7]1)=[O:12])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 5

HCID 180Acetone2×HCID 313Hydrochloric Acid2×HCID 962WaterHCID 516875Potassium PermanganateHCID 86637297HCID 86637297, compound

Product 1

HCID 68731899HCID 68731899, compound

Conditions

Temperature
15 °C

Procedure

Benzyl 3-(1,1-dimethyl-2-oxoethyl)-3-hydroxypyrrolidine-1-carboxylate (12.70 g, 0.04359 mol) was dissolved in acetone (179.5 mL, 2.444 mol) and cooled to 15° C. and 1.0 M of hydrogen chloride in water (65.39 mL, 0.06539 mol) was added dropwise. After addition of the HCl was complete, a solution of potassium permanganate (11.0 g, 0.0697 mol) in acetone (493.6 mL, 6.722 mol) was added dropwise. The reaction mixture was stirred at room temperature for 6 h, filtered and the filter cake was washed with acetone. The filtrate was evaporated, in vacuo, diluted with methylene chloride, dried, filtered and the solvent was evaporated, in vacuo, to provide a crude product which was used directly in next step. LCMS (M+H) 308.2.

Workup

  1. filtrationfiltered
  2. washthe filter cake was washed with acetone
  3. customThe filtrate was evaporated, in vacuo
  4. additiondiluted with methylene chloride
  5. customdried
  6. filtrationfiltered
  7. customthe solvent was evaporated, in vacuo

Sources & evidence

ORD record
ord-c79fd8e8f5ee4257ae460465debae800
Source dataset
uspto-grants-2012_11
Patent number
US08309718B2

Reaction notes

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