Sodium Bicarbonate → 1-cyclopentyl N-{3-[(methylamino)methyl]benzyl}-L-leucinate

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To a solution of 3-(bromomethyl)-benzaldehyde (0.513 g, 2.57 mmol) in dichloroethane (10 mL) was added L-leucine cyclopentyl ester tosylate (1.29 g, 3.46 mmol) and sodium triacetoxyborohydride (1.37 g, 6.46 mmol). The mixture was stirred for 30 minutes at room temperature then poured into ethyl acetate (200 mL). The organic extracts were washed with saturated ammonium chloride (2 times 50 mL) and water (50 mL). The organic extracts were then dried (MgSO4) and concentrated. The residue was dissolved in ethanol (30 mL) and methylamine hydrochloride (4.17 g, 61.7 mmol) was added followed by sodium hydrogen carbonate (4.32 g, 51 mmol). The mixture was stirred at room temperature for 18 hours then concentrated under vacuum, loaded directly onto a silica gel column and eluted with 95:5 dichloromethane:methanol to yield the desired product (0.130 g, 15% yield). LC/MS: m/z 333.25 [M+H]+

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