Triethylamine → (R)-N-(2,2-dimethoxyethyl)pentan-2-amine

2,2-Dimethoxyacetaldehyde (0.59 mL) was added to a solution of (R)-pentan-2-amine hydrochloride (0.48 g) and triethylamine (0.54 mL) in methanol (4 mL) and the mixture stirred for 2 h. A slurry of palladium on carbon (10%, 20 mg) in methanol (1 mL) was added and the mixture hydrogenated at 5 bar for 20 h. The mixture was then filtered and in vacuo. The resulting residue was triturated with diethyl ether (5 mL) and the resulting white solid extracted with further diethyl ether (2×5 mL). The combined ether fractions were concentrated in vacuo to afford (R)—N-(2,2-dimethoxyethyl)pentan-2-amine (0.745 g) as an oil. 1H NMR (400 MHz, CDCl3) δ 4.92 (t, J=5.4 Hz, 1H), 3.47 (s, 3H), 3.47 (s, 3H), 3.25-3.15 (m, 1H), 2.99 (ddd, J=27.9, 12.7, 5.5 Hz, 2H), 1.86-1.77 (m, 1H), 1.64-1.54 (m, 1H), 1.49-1.32 (m, 5H), 0.95 (t, J=7.3 Hz, 3H)

1. waitthe mixture hydrogenated at 5 bar for 20 h
2. filtrationThe mixture was then filtered and in vacuo
3. customThe resulting residue was triturated with diethyl ether (5 mL)
4. extractionthe resulting white solid extracted with further diethyl ether (2×5 mL)
5. concentrationThe combined ether fractions were concentrated in vacuo

ORD record

ord-9796064ded7d41839f1826af1cff3fc5

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08017602B2