Trimethylsilylacetylene → HCID 14115006, compound

(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).

1. additionwas added dropwise via an addition funnel
2. customwas recooled to 0 ° C.
3. customcannulated to a 0° C.
4. stirringThe resulting solution was stirred for 20 h at RT
5. temperatureThe reaction mixture was cooled to 0° C.
6. customquenched with sat. NH4Cl
7. customthe organic solvent removed
8. customThe residue was partitioned between EtOAc and H2O
9. washThe organic layer was washed with sat. NaHCO3, brine
10. dry with materialdried over MgSO4
11. concentrationconcentrated
12. customThe residue was purified by SiO2 (90% hexanes: 10% acetone)

ORD record

ord-d81068d1c5ae46eea89c50f79edfffe0

Source dataset

uspto-grants-2008_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07414134B2