Potassium bis(trimethylsilyl)amide → (S)-3-Vinyl-3,4-dihydro-1H-isoquinoline-2-carboxylic Acid Tert-butyl Ester

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Reaction Steps

To a solution of methyltriphenylphosphonium bromide (2.07 g, 5.8 mmol) in THF (20 mL) at −78° C. is added KHMDS (11.0 mL, 5.5 mmol) and the mixture is stirred for 1.5 h. A solution of (S)-3-formyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (0.94 g, 3.6 mmol) in THF (10 mL) is added and the solution stirred at −78-C for 1.5 h before warming to RT. The reaction is quenched with water (10 mL) and extracted with EtOAc (2×30 mL). The organic extracts are washed with 1N HCl (3×35 mL), brine (2×30 mL) and dried over Na2SO4. Purification by flash chromatography using a gradient of 0-15% EtOAc/hexane affords the title compound.

Provenance & Evidence