Allyltrimethylsilane → (2S,5R)-5-Allyl-1-methyl-pyrrolidine-2-carboxylic acid phenethyl-amide

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Reaction Steps

A dichloromethane (20 mL) solution of 11C methylaminal (7.7 g, 20 mmol) is chilled to −78° C. After 20 minutes, allyltrimethylsilane (6.5 mL, 40 mmol) is added. After 10 more minutes 1 M titanium(IV) chloride (24 mL, 24 mmol) is added slowly by syringe. The reaction is complete after 1 hour. The resulting material is carefully quenched (frothing) with saturated bicarb and extracted with dichlormethane, then washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The product is isolated by flash chromatography (SiO2), and it crystallizes upon standing. LCMS characterization ES+393.1 (m+1).

Provenance & Evidence