Triethylamine → HCID 86638743, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (±)-phenylmethyl 4-(1-hydroxyethyl)-1-piperidinecarboxylate (0.64 g, 2.43 mmol), Et3N (1.03 mL, 7.29 mmol) in CH2Cl2 (50 mL) at 0° C. was treated dropwise with methanesulfonyl chloride (0.38 mL, 4.86 mmol). The reaction mixture was stirred at 0° C. for 1 h, then at ambient temperature for 1.5 h, diluted with CH2Cl2 (100 mL) and washed with 1M NaH2PO4 (50 mL×2) and brine (25 mL). The CH2Cl2 layer was dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product as a light brown oil. The crude product was purified by flash chromatography on an ISCO silica gel column using 0 to 45% EtOAc/hexanes to give 0.73 g (88%) of (±)-phenylmethyl 4-{1-[(methylsulfonyl)oxy]ethyl}-1-piperidinecarboxylate as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.40-7.25 (m, 5H), 5.12 (s, 2H), 4.70-4.60 (m, 1H), 4.25 (bs, 2H), 2.99 (s, 3H), 2.80-2.65 (m, 2H), 1.85-1.60 (m, 3H), 1.40 (d, 3H, J=6.4 Hz), 1.35-1.20 (m, 2H).

Provenance & Evidence