3,3-Dimethylbutanal → HCID 53751206, compound

Participants

Reaction Steps

Sodium hydrogen carbonate (1.68 g, 0.02 mol) was added to a Parr bottle containing a solution of dimethyl L-aspartate hydrochloride (3.94 g, 0.02 mol) in water (10 mL), followed by addition of 3,3-dimethylbutyraldehyde (2.2 g, 0.02 mol) in methanol (100 mL) and Pd/C (4% palladium on carbon, 50% wet), 10% by weight of substrate. The mixture was hydrogenated at 50 psi at room temperature for 1.5 hrs then filtered through a Celite® bed and the bed washed with methanol (10 mL). The filtrate and washings were concentrated under reduced pressure. The residual aqueous solution was extracted with diethyl ether (2×100 mL). The organic layer was washed with aqueous saturated sodium hydrogen carbonate solution (50 mL), dried over anhydrous magnesium sulfate, filtered and concentrated to give N-neohexyl-L-aspartic acid dimethyl ester (4.65 g, 95%) as an oil. NMR (CDCl3) δ3.67 (s, 3H); 3.50 (s, 3H); 3.57(t, 3H); 2.37-2.70 (m, 4H); 1.20-1.40 (m, 2H); 0.80 (s, 9H).

Provenance & Evidence