Dihydroxyacetone → 2-((1,3-Dihydroxypropan-2-yl)amino)propane-1,3-diol

In an autoclave, a mixture of serinol (10.6 g, 0.12 mol), 1,3-dihydroxyacetone (10.4 g, 0.12 mol), and Raney nickel (1 g, wet) in methanol (100 ml) was heated to 65° C. under 250 psi hydrogen pressure for 3 h. The autoclave was cooled to ambient temperature and depressurized. The resulting reaction mixture was filtered to remove the catalyst. The filtrate was evaporated under vacuum to remove ammonia and most of the water. The residue was dissolved in a 1:1 mixture of 2-butanol and tetrahydrofuran, treated with activated carbon, and evaporated to give the bis-adduct 2,2′-iminobis-1,3-propanediol as a viscous oil (15 g, 79%). Assay by GC: 99%.

1. customThe resulting reaction mixture
2. filtrationwas filtered
3. customto remove the catalyst
4. customThe filtrate was evaporated under vacuum
5. customto remove ammonia
6. dissolutionThe residue was dissolved in a 1:1 mixture of 2-butanol and tetrahydrofuran
7. additiontreated with activated carbon
8. customevaporated

ORD record

ord-f1810db1922e409eb2041b56b26a981f

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08653306B1