Trimethylsilyl iodide → methyl (5R)-5-((trimethylsilyl)ethynyl)-L-prolinate

HRID 855809Notes

Reaction equation

HRID 855809 reaction equation
[CH3:1][Si:2]([C:5]#[C:6][C@@H:7]1[N:11](C(OC)=O)[C@H:10]([C:16]([O:18][CH3:19])=[O:17])[CH2:9][CH2:8]1)([CH3:4])[CH3:3].I[Si](C)(C)C>C(Cl)(Cl)Cl>[CH3:1][Si:2]([C:5]#[C:6][C@@H:7]1[NH:11][C@H:10]([C:16]([O:18][CH3:19])=[O:17])[CH2:9][CH2:8]1)([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 11161884dimethyl(2S,5R)-5-((trimethylsilyl)ethynyl)pyrrolidine-1,2-dicarboxylate

Product 1

HCID 16090847methyl (5R)-5-((trimethylsilyl)ethynyl)-L-prolinate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of dimethyl(2S,5R)-5-((trimethylsilyl)ethynyl)pyrrolidine-1,2-dicarboxylate (5.43 g, 19.16 mmol) and iodotrimethylsilane (3 mL, 28.74 mmol) in chloroform (100 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 226 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-188e1c0f9bac4061856ed66dcb52bd2a
Source dataset
uspto-grants-2007_08
Patent number
US07262207B2

Reaction notes

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