Trimethylsilylacetylene → HCID 69377678, compound

Temperature

-78 °C

A solution of trimethylsilyl acetylene at −78° C.(4.14 g, 0.042 mol) in THF (60 mL) was treated with n-butyl lithium (29 mL, 0.042 mol; 1.6 M solution in THF). The resulting mixture was stirred at −78° C. for 15 min. A solution of N-4-Boc-aminocyclohexanone (3 g, 0.014 mol; Astatech, Inc) in THF (120 mL) was added dropwise over a period of 30 min. The resulting mixture was stirred at −78° C. for 1 h and then allowed to slowly warm up to room temperature over 1 h. The reaction was quenched with a saturated solution of ammonium chloride and diluted with EtOAc and washed with saturated aqueous NaHCO3 solution, H2O, and saturated aqueous NaCl solution. The organic layer was dried over MgSO4 and concentrated to yield an off-white foam (4.38 g, 100%).

1. stirringThe resulting mixture was stirred at −78° C. for 1 h
2. temperatureto slowly warm up to room temperature over 1 h
3. customThe reaction was quenched with a saturated solution of ammonium chloride
4. additiondiluted with EtOAc
5. washwashed with saturated aqueous NaHCO3 solution, H2O, and saturated aqueous NaCl solution
6. dry with materialThe organic layer was dried over MgSO4
7. concentrationconcentrated

ORD record

ord-316978f2d73e42949b7719b9953c6bee

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07141564B2