1,3-Oxazolidine → HCID 55284965, compound

Temperature

40 °C

Catalytic hydrogenation of the 2-methyl-2-nitro-3-heptanol to the 2-amino-2-methyl-3-heptanol. A sample of 2-amino-2-methyl-3-heptanol (2A2M3H) was synthesized by the reduction of the 2-methyl-2-nitro-3-heptanol by a Parr Autoclave unit. The stainless steel, 2 liter autoclave was loaded with Grace 3201 Raney Nickel (RaNi, 90 g wet, 45 g dry, 10 wt %) and methanol (MeOH, 300 g). The autoclave was sealed, assembled, purged with nitrogen then hydrogen, pressurized with hydrogen, stirred at 600 RPM, and warmed to 40° C. The yellow nitro-alcohol (422 g) had been diluted with absolute ethanol (EtOH, 150 g) and was pumped into the autoclave (4 ml/min) After 3 h the addition was complete and after 3.5 h the reaction was judged complete as no hydrogen uptake was observed. The autoclave was cooled, stirring stopped, vented, and purged with nitrogen. The autoclave was disassembled and the contents were vacuum filtered to remove the RaNi catalyst. This resulted in the isolation of a light yellow liquid (80 area %) that was concentrated in vacuo (55° C./full vacuum) before product was taken overhead (50-52° C./full vacuum). This resulted in the isolation of a clear, colorless, solid (268 g, 91.9 area %, 57% overall yield) that contained some oxazolidine (4.9 area %).

1. customThe autoclave was sealed
2. custompurged with nitrogen
3. additionThe yellow nitro-alcohol (422 g) had been diluted with absolute ethanol (EtOH, 150 g)
4. additionthe addition
5. waitwas complete and after 3.5 h
6. temperatureThe autoclave was cooled
7. stirringstirring
8. custompurged with nitrogen
9. filtrationfiltered
10. customto remove the RaNi catalyst
11. customThis resulted in the isolation of a light yellow liquid (80 area %) that
12. concentrationwas concentrated in vacuo (55° C./full vacuum) before product
13. custom(50-52° C./full vacuum)
14. customThis resulted in the isolation of a clear, colorless,
15. customsolid (268 g, 91.9 area %, 57% overall yield) that

ORD record

ord-5c850a0fb2714c8ab8ac87af951d475c

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09034929B2