9-Fluorenylmethyl chloroformate → 4-(9H-fluoren-9-ylmethyl) 3-methyl 3,4-morpholinedicarboxylate

Participants

Reaction Steps

To a stirred solution of methyl morpholine-3-carboxylate hydrochloride (2.0 g, 11.01 mmol) in a mixture of 1,4-dioxane (10 mL) and water (20 mL) was added sodium bicarbonate (2.79 g, 33.2 mmol). The suspension was cooled in an ice-water bath and a solution of Fmoc chloride (2.93 g, 11.33 mmol) in 1,4-dioxane (30 mL) was added. The mixture was stirred at ambient temperature for 2 hours. The mixture was partitioned between ethyl acetate (150 mL) and water (150 mL). The phases were separated and the organic extract washed with 1 M aqueous HCl (150 mL) and brine (50 mL). The organic extract was dried (MgSO4), filtered and the solvent removed in vacuo to leave a colourless gum, 4.2 g. LCMS [LCMS4] Rt 3.10 min, m/z (ES+) 368 (M+H).

Provenance & Evidence