Trimethylsilyl iodide → methyl (5R)-5-propenyl-L-prolinate

HRID 1642718Notes

Reaction equation

HRID 1642718 reaction equation
[C:1]([C@@H:4]1[N:8](C(OC)=O)[C@H:7]([C:13]([O:15][CH3:16])=[O:14])[CH2:6][CH2:5]1)#[C:2][CH3:3].I[Si](C)(C)C>C(Cl)(Cl)Cl>[CH:1]([C@@H:4]1[NH:8][C@H:7]([C:13]([O:15][CH3:16])=[O:14])[CH2:6][CH2:5]1)=[CH:2][CH3:3]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 66756906dimethyl(2S,5R)-5-propynyl-pyrrolidine-1,2-dicarboxylate

Product 1

HCID 66756839methyl (5R)-5-propenyl-L-prolinate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of dimethyl (2S,5R)-5-propynyl-pyrrolidine-1,2-dicarboxylate (4.25 g, 18.90 mmol) and iodotrimethylsilane (3.23 mL, 22.7 mmol, Example 85A) in chloroform (60 mL) was heated to 65° C. for 3 hours, was cooled to room temperature, concentrated under reduced pressure and flash chromatographed with 35% ethyl acetate/65% hexane to provide the titled compound. MS (DCI/NH3) m/e 168 (M+H)+.

Workup

  1. concentrationconcentrated under reduced pressure and flash
  2. customchromatographed with 35% ethyl acetate/65% hexane

Sources & evidence

ORD record
ord-dbce47a10b434b0084326f1bf82d164e
Source dataset
uspto-grants-2012_02
Patent number
US08119664B2

Reaction notes

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