Triethylamine → HCID 66672731, compound

Participants

Reaction Conditions

Reaction Steps

Methanesulfonyl chloride (0.28 mL, 3.6 mmol) was added dropwise to a solution of 1-methylethyl 4-(hydroxymethyl)-1-piperidinecarboxylate (prepared as in Example 9, Step 1, 600 mg, 3 mmol), triethylamine (0.627 mL, 4.5 mmol), and CH2—Cl2 (10 mL) at 0° C. The mixture was stirred at 0° C. for 30 min, then at ambient temperature for 2 h. The mixture was washed with water, and the organics were concentrated. The resulting crude material was mixed with 4-bromobenzenethiol (567 mg, 3 mmol) and K2CO3 (829 mg, 6 mmol) in DMF (10 mL), and the mixture was stirred at ambient temperature overnight. The mixture was charged with water, and extracted with EtOAc. The organics were dried over MgSO4, filtered, and the filtrate was concentrated. The crude product was purified by chromatography on a silica gel column using 0 to 10% EtOAc/hexanes to give 292 mg (26%) of 1-methylethyl 4-{[(4-bromophenyl)thio]methyl}-1-piperidinecarboxylate as a clear oil. 1H NMR (400 MHz, CDCl3): δ 7.37 (d, 2H, J=8.5 Hz), 7.15 (d, 2H, J=8.5 Hz), 4.95-4.82 (m, 1H), 4.15-4.09 (m, 2H), 2.80 (d, 2H, J=6.9 Hz), 2.72-2.60 (m, 2H), 1.85-1.77 (m, 2H), 1.70-1.60 (m, 1H), 1.24-1.08 (m, 8H); LRMS (ESI), m/z 372/374 (M+H).

Provenance & Evidence