Magnesium → HCID 69428791, compound

HRID 458310Notes

Reaction equation

HRID 458310 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 69428532HCID 69428532, compound

Product 1

HCID 69428791HCID 69428791, compoundYield 110.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In analogy to literature [Hudlicky, T.; Sinai-Zingde, G.; Natchus, M. G. Tetrahedron Lett. (1987), 28(44), 5287–90] a solution of 0.35 g (0.84 mmol) (2S,4R)-2-(2-ethoxycarbonyl-vinyl)-4-(4-methoxy-benzylsulfanyl)-pyrrolidine-1-carboxylic acid tert-butyl ester in 20 ml MeOH was treated with 0.122 g (5.04 mmol) magnesium and stirred at room temperature for 5 h. The reaction was evaporated, suspended twice in EtOAc and filtered to give 0.38 g (quantitative) of (2R,4R)-4-(4-methoxy-benzylsulfanyl)-2-(2-methoxycarbonyl-ethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester, MS: 410 (MH+).

Workup

  1. customThe reaction was evaporated
  2. filtrationfiltered

Sources & evidence

ORD record
ord-af59c52e2d264758a9f3a89b06750263
Source dataset
uspto-grants-2007_03
Patent number
US07189756B2

Reaction notes

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