Lithium Hexamethyldisilazide → HCID 57794742, compound

Participants

Reaction Conditions

Reaction Steps

To (1R)-3-cyano-3-phenyl-1-{[(phenylmethyl)oxy]methyl}propyl 4-methylbenzenesulfonate (7.4 g, 17.0 mmol), accessed via the method of preparation 2, in 70 mL DMF at −42° C. was added 1M lithium bis(trimethylsilyl)amide in hexanes (25.5 mL, 25.5 mmol, 1.5 eq) dropwise and stirred with continued cooling at −42° C. for 1 h. The reaction mixture was diluted with EtOAc, washed successively with water (4×) and brine, dried over MgSO4, filtered and concentrated to give the title compound (4.25 g, 16.1 mmol, 95%) as a yellow oil which was shown to be a 94:6 mix of the title compound to the product of Preparation 3B. 1H NMR (300 MHz, CDCl3) δ 7.42-7.29 (m, 10H), 4.64 (m, 2H), 3.91-3.86 (m, 1H), 3.74-3.68 (m,1H), 2.00-1.90 (m, 1H), 1.68-1.56 (m, 2H).

Provenance & Evidence