Acetaldehyde, 2,2-dimethoxy- → (R)-N-(2,2-dimethoxyethyl)-3-methylbutan-2-amine

2,2-Dimethoxyacetaldehyde (60% in water, 8.7 mL) was added to (R)-3-methylbutan-2-amine (5.0 g) in methanol (25 mL) and the mixture stirred at ambient temperature overnight. A slurry of palladium on carbon (5%, 1.2 g) in water (10 mL) was added and the mixture was hydrogenated at 5 bar pressure with stirring for 3 hours. The mixture was filtered through Celite and the filter pad washed with methanol (3×100 mL). The combined filtrate and washings were concentrated to a volume of −10 mL and then toluene (200 mL) was added. The mixture was concentrated, more toluene (200 mL) was added and the mixture was concentrated once more to give the titled compound as a yellow oil. Yield 8.0 g.

1. stirringwith stirring for 3 hours
2. filtrationThe mixture was filtered through Celite
3. washthe filter pad washed with methanol (3×100 mL)
4. concentrationThe combined filtrate and washings were concentrated to a volume of −10 mL
5. additiontoluene (200 mL) was added
6. concentrationThe mixture was concentrated
7. additionmore toluene (200 mL) was added
8. concentrationthe mixture was concentrated once more

ORD record

ord-c34d7136e8a947fabcca2f9a39f2bafe

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476265B2