Sodium Hydroxide → tert-Butyl 4-(3-hydroxypropyl)tetrahydro-1(2h)-pyridinecarboxylate

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Reaction Steps

A stirred solution of 3-2 (41.8 g, 0.14 mol), dioxane (300 mL), and 3N NaOH (0.51 mol, 170 mL) at ambient temperature was treated with di-butyl dicarbonate (32.1 g, 0.15 mol). After 24 h the dioxane was evaporated and the aqueous phase extracted with ether. The ethereal extracts were combined, washed with 10% KHSO4 and brine, dried (MgSO4), and then concentrated. Flash chromatography (silica, 30% to 50% EtOAc/ hexanes) gave 3-3 as an oil, Rf 0.11 (silica, 20% EtOAc/hexanes).

Provenance & Evidence