Hydrochloric Acid → HCID 86584545, compound

Participants

Reaction Steps

R-2-Methyl-CBS-oxazaborolidine (1.0 M in THF, 2 mL, 2 mmol) in 50 mL of THF was added slowly to a stirred solution of borane-THF complex (1.0 M in THF, 12 mL, 12 mmol) at room temperature. The mixture was stirred for 30 minutes and then N-(5-bromoacetyl-2-chloro-phenyl)-methanesulfonamide (which was obtained in Example 24) (2.80 g, 8.6 mmol) in 50 mL of THF was added dropwise. Upon stirring over night hydrochloride (1.0 M solution in diethyl ether) was added until the pH was ˜1. After stirring for one hour the reaction mixture was partitioned between ethyl acetate and water. The organic phase was dried over MgSO4 and concentrated. The residue was then dissolved in 50 mL of DMSO. To the solution sodium azide (2.93 g, 45 mmol) and sodium iodide (3 g, 20 mmol) were added. After stirring at room temperature for 3 days the reaction was quenched with water, extracted with diethyl ether. The organic layer was dried over MgSO4 and concentrated. The product was purified by flash silica gel chromatography eluting with ethyl acetate and hexanes to give the title compound as a white solid (1.6 g, 64%); 1H NMR (300 MHz, CDCl3) δ 2.60 (d, J=5.9 Hz, 1H), 3.06 (s, 3H), 3.45-3.50 (m, 2H), 4.85-4.95 (m, 1H), 6.84 (brs, 1H), 7.22 (dd, J=8.3, 2.0 Hz, 1H), 7.44 (d, J=8.3 Hz, 1H), 7.65 (d, J=2.0 Hz, 1H); MS (ES) m/z: 288.9 ((M−H)−, 100%); HRMS Calcd. for C9H12ClN4O3S(M+): 290.0241. Found: 290.0228.

Provenance & Evidence