Tetrahydrofuran → HCID 178453956, compound

Participants

Reaction Conditions

Reaction Steps

Methyl trans-4-(tert-butoxycarbonylamino)cyclohexanecarboxylate (55.5 g, 216 mmol) is suspended in ethanol (900 mL) and THF (100 mL) and the mixture is cooled to 5° C. Granular calcium chloride (47.9 g, 431 mmol) is added portionwise to give a milky suspension. Sodium borohydride (32.6 g, 863 mmol) is added portionwise over 25 mins at 5° C. The reaction mixture (white emulsion) is stirred at 5° C. for 1 hour, the water bath is removed and then the reaction mixture is allowed to warm to room temperature and stirred at room temperature overnight. The reaction mixture is cooled to 10° C. and 5% potassium carbonate (200 mL) is added dropwise until the pH of the solution is pH11. A colourless precipitate formed which is filtered off. The solid is stirred with ethyl acetate (2000 mL) and water (500 mL). The organic layer is separated and washed with 0.5M HCl (200 mL), then washed with water (2×200 mL) and saturated brine (100 mL). The organic solution is dried over anhydrous MgSO4, filtered and evaporated to give a white solid. The solid is dried under high vacuum overnight to constant weight; [MH+230].

Provenance & Evidence