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To a −78° C. solution of oxalyl chloride (5.1 mL, 57 mmol) in dichloromethane (100 mL) in an oven-dried round-bottomed flask was added dimethylsulfoxide (8.2 mL, 114 mmol) in dichloromethane (17 mL). The mixture was stirred for 2 minutes and tert-butyl 4-(chloromethyl)-4-(hydroxymethyl)piperidine-1-carboxylate (13.7 g, 52 mmol) in dichloromethane (50 mL) was added over 10 minutes. The solution was stirred for 15 minutes at −78° C. and triethylamine (36 mL, 260 mmol) was added. The mixture was stirred at −78° C. for 15 minutes and was warmed to room temperature. The mixture was stirred for 15 minutes at room temperature and was quenched with saturated aqueous NaHCO3 (200 mL). The aqueous solution was washed with Et2O (2×300 mL). The combined organic layers were washed with brine, dried (Na2SO4) and concentrated under reduced pressure to give the title compound (SM-3a) as a yellow oil that solidified upon standing under nitrogen atmosphere at room temperature (13.7 g, 99%). 1H NMR (CDCl3) δ 1.43 (s, 9H), 1.48-1.60 (m, 2H), 2.00-2.07 (m, 2H), 3.07 (t, 2H), 3.57 (s, 2H), 3.69-3.79 (m, 2H), 9.55 (s, 1H).

1. stirringThe solution was stirred for 15 minutes at −78° C.
2. stirringThe mixture was stirred at −78° C. for 15 minutes
3. stirringThe mixture was stirred for 15 minutes at room temperature
4. customwas quenched with saturated aqueous NaHCO3 (200 mL)
5. washThe aqueous solution was washed with Et2O (2×300 mL)
6. washThe combined organic layers were washed with brine
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated under reduced pressure