Magnesium → HCID 69428791, compound

HRID 1264381Notes

Reaction equation

HRID 1264381 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([S:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH2:10][C@H:9]1/[CH:23]=[CH:24]\[C:25]([O:27][CH2:28]C)=[O:26])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Mg]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([S:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)[CH2:10][C@H:9]1[CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 5462224MagnesiumHCID 70003300HCID 70003300, compound

Product 1

HCID 69428791HCID 69428791, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.78 g (9 mmol, 1eq) (E)- and/or (Z)-(2S,4R)-2-(2-Ethoxycarbonyl-vinyl)-4-(4-methoxy-benzylsulfanyl)-pyrrolidine-1-carboxylic acid tert-butyl ester in 42 ml MeOH were treated with 1.32 g (54 mmol, 6 eq) magnesium at RT for 5 h. The solvent was evaporated, the crude product dissolved in EtOAc and filtered from the solid particles. This process was repeated, the solvent evaporated yielding 3.67 g (quant) (2R,4R)-4-(4-Methoxy-benzylsulfanyl)-2-(2-methoxycarbonyl-ethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester as colorless oil, MS: 410 (MH+).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe crude product dissolved in EtOAc
  3. filtrationfiltered from the solid particles
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-d953f92bea0640c7ba9e4dd30e80590e
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

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