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

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.

1. stirringthe solution stirred at −78-C for 1.5 h
2. customThe reaction is quenched with water (10 mL)
3. extractionextracted with EtOAc (2×30 mL)
4. washThe organic extracts are washed with 1N HCl (3×35 mL), brine (2×30 mL)
5. dry with materialdried over Na2SO4
6. customPurification by flash chromatography

ORD-Eintrag

ord-60f5df8fe4294b20a5e9b54781c9bcba

Quelldatensatz

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08084448B2