Isopropanol → HCID 15117319, compound

HRID 1029673Notes

Reaction equation

HRID 1029673 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][CH:10]([CH:12]([OH:14])[CH3:13])[CH2:9][C@H:8]1[CH2:15][OH:16])=[O:6])[CH:2]=[CH2:3].CC(C)=[O:19].OS(O)(=O)=O.O=[Cr](=O)=O.CC(O)C>CC(C)=O>[C:12]([CH:10]1[CH2:11][N:7]([C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])[C@H:8]([C:15]([OH:19])=[O:16])[CH2:9]1)(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 15117318HCID 15117318, compoundHCID 131709961Jones' reagent

Product 1

HCID 15117319HCID 15117319, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of (2S)-1-allyloxycarbonyl-4-(1-hydroxyethyl)-2-hydroxymethylpyrrolidine (30 g) in acetone (300 ml) was added dropwise Jones' Reagent (2.67N, 245 ml) at 0° C. After stirring for 3 hours, to the reaction mixture was added dropwise 2-propanol (500 ml), and the mixture was stirred at 0° C. for 1 hour. The precipitate was filtered off and the filtrate was evaporated to give a residual oil, which was extracted with ethyl acetate and the organic layer was separated, washed with brine, dried over magnesium sulfate. Evaporation of the solvent gave (2S)-4-acetyl-1-allyloxycarbonylpyrrolidine-2-carboxylic acid (26.56 g).

Workup

  1. stirringthe mixture was stirred at 0° C. for 1 hour
  2. filtrationThe precipitate was filtered off
  3. customthe filtrate was evaporated
  4. customto give a residual oil, which
  5. extractionwas extracted with ethyl acetate
  6. customthe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried over magnesium sulfate
  9. customEvaporation of the solvent

Sources & evidence

ORD record
ord-5d382b2415444d3a9a2fa68af6e13252
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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