Trimethylsilylacetylene → HCID 14115006, compound

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Reaction Steps

(Trimethylsilyl)acetylene (5.8 mL, 41.65 mmol) was dissolved in 15 mL dry TMEDA and cooled to 0° C. n-BuLi (12.50 mL, 31.24 mmol) was added dropwise via an addition funnel and the resulting mixture was stirred for 20 min at RT. The solution was recooled to 0 ° C. and cannulated to a 0° C. solution of (S)-2-methyl-1-(4-methylbenzenesulfonyl)aziridine (2.2 g, 10.4 mmol) in 15 mL TMEDA . The resulting solution was stirred for 20 h at RT. The reaction mixture was cooled to 0° C. and quenched with sat. NH4Cl and the organic solvent removed. The residue was partitioned between EtOAc and H2O. The organic layer was washed with sat. NaHCO3, brine, dried over MgSO4 and concentrated. The residue was purified by SiO2 (90% hexanes: 10% acetone) to afford the title compound. MS (m/z): 310.2 (M+H) (Calc'd for C15H23NO2SSi: 309.5).

Provenance & Evidence