Ethyl Acetate → HCID 68681559, compound

HRID 1441722Notes

Reaction equation

HRID 1441722 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH2:25][CH:26]=[CH2:27])[CH2:9][CH:8]([O:10][Si](C(C)(C)C)(C)C)[CH2:7][N:6]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:4].CCCC[N+](CCCC)(CCCC)CCCC.[F-].CCOC(C)=O>C1COCC1>[CH3:1][O:2][C:3]([C@@:5]1([CH2:25][CH:26]=[CH2:27])[CH2:9][C@@H:8]([OH:10])[CH2:7][N:6]1[C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])=[O:4]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 85375464HCID 85375464, compound

Product 1

HCID 68681559HCID 68681559, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3.3 g (8.27 mmol) (2R,4R)-(2-allyl-4-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester are dissolved in 60 mL THF, cooled below 5° C. and treated with 8.68 mL (1.05 eq) 1 M TBAF in THF under stirring. The reaction mixture is allowed to slowly reach room temperature, while being stirred another 4 h. Ice and AcOEt are added, the mixture washed with brine twice, and the organic phase evaporated to yield a crude product which is column chromatographed (silica gel, TBME/petroleum ether 1:1) to yield 1.8 g desired product as a colorless, thick oil, which is used as such in the next step.

Workup

  1. temperaturecooled below 5° C.
  2. customis allowed to slowly reach room temperature
  3. stirringwhile being stirred another 4 h
  4. washthe mixture washed with brine twice
  5. customthe organic phase evaporated
  6. customto yield a crude product which
  7. customchromatographed (silica gel, TBME/petroleum ether 1:1)

Sources & evidence

ORD record
ord-75a02af5dda34c56b4fbde04d0ce0282
Source dataset
uspto-grants-2010_02
Patent number
US07655686B2

Reaction notes

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