Sodium Cyanide → HCID 21224101, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-benzyl-4-[4-(4-chlorophenoxy)-phenylsulfonylmethyl]-tetrahydropyran-4-carboxylic acid methyl ester (410 mg, 0.80 mmol) in N,N-dimethylformamide (4 mL) was added lithium iodide (1.06 g, 7.96 mmol), followed by sodium cyanide (78 mg, 1.59 mmol). The mixture was heated to 120° C. for 8 hours, cooled to room temperature, the N,N-dimethylformamide solvent removed by heating under reduced pressure, and the residue partitioned between ethyl acetate (150 mL) and saturated aqueous sodium bisulfite (50 mL). The ethyl acetate layer was dried over magnesium sulfate, concentrated in vacuo, purified by preparative chromatography (20×40-1000 um plates), eluted with 8% methanol/methylene chloride) to afford 317 mg (80%) of 3-benzyl-4-[4-(4-chlorophenoxy)-phenylsulfonylmethyl]-tetrahydropyran-4-carboxylic acid 1HNMR (N,N-dimethylformamide contaminant, CDCl3) δ 1.74 (dm, J=13.5 Hz, 1H), 2.05-2.18 (m, 2H), 2.42 (dm, J=13.5 Hz, 1H), 3.22-3.26 (m, 2H), 3.48-3.58 (m, 2H), 3.78-4.18 (m, 5H), 6.83-6.88 (m, 4H), 6.93 (d, J=8.5 Hz, 2H), 7.08-7.13 (m, 3H), 7.36 (d, J=8.7 Hz, 2H), 7.62 (d, J=8.7 Hz, 2H); CIMS (NH3, M+ +NH4 +): 518.

Provenance & Evidence