3,3-Dimethylbutanal → HCID 53751206, compound

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).

1. filtrationthen filtered through a Celite® bed
2. washthe bed washed with methanol (10 mL)
3. concentrationThe filtrate and washings were concentrated under reduced pressure
4. extractionThe residual aqueous solution was extracted with diethyl ether (2×100 mL)
5. washThe organic layer was washed with aqueous saturated sodium hydrogen carbonate solution (50 mL)
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-34dfd9dce9f0452e8e2dc3f1b692d479

Source dataset

uspto-grants-2000_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06077962