Acetaldehyde, 2,2-dimethoxy- → (R)-N-(2,2-Dimethoxyethyl)hexan-2-amine

2,2-Dimethoxyacetaldehyde (7.54 mL) was added to a solution of (R)-hexan-2-amine (5.06 g) in methanol (20 mL) and the mixture stirred at ambient temperature for 5 h. A slurry of 10% palladium on carbon (200 mg) in methanol (5 mL) was added and the mixture hydrogenated at 5 bar for 16 h, then filtered and concentrated in vacuo to afford the sub-titled compound as a colourless liquid (9.22 g). 1H NMR (400 MHz, CDCl3) δ 4.46 (t, J=5.5 Hz, 1H), 3.39 (s, 6H), 2.72 (ddd, J=31.1, 11.9, 5.6 Hz, 2H), 2.60 (sextet, J=6.0 Hz, 1H), 1.36-1.24 (m, 6H), 1.04 (d, J=6.2 Hz, 3H), 0.90 (t, J=6.9 Hz, 3H)

1. waitthe mixture hydrogenated at 5 bar for 16 h
2. filtrationfiltered
3. concentrationconcentrated in vacuo

ORD record

ord-e1854d4cb35048878891e53f7d7a2305

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08017602B2