Hydroxyamine hydrochloride → HCID 24774027, compound

Temperature

100 °C

To a flask containing (5R)-1-azabicyclo[3.2.1]octan-3-one hydrochloride (3.64 g, 22.6 mmol), hydroxylamine hydrochloride (2.04 g, 29.4 mmol), and ethanol (130 mL) was added sodium acetate trihydrate (9.23 g, 67.8 mmol). The mixture stirred for 3 h and was filtered and concentrated. The resulting white solid was taken up in n-propanol (100 mL) and sodium (˜13.6 g, 618 mmol) was added over 20–25 portions. The reaction spontaneously began to reflux, and the reaction was heated in an oil bath (100° C.). The addition was complete in ˜20 min and the mixture had solidified after ˜40 min. The oil bath was removed and n-propanol (2×25 mL) was added dissolving the remaining sodium metal. The mixture was carefully quenched through the dropwise addition of H2O (100 mL). Saturated aq. NaCl (20 mL) was added, and the layers were separated. The organic layer was dried (MgSO4), filtered, treated with freshly prepared MeOH/HCl, and concentrated. The resulting solid was triturated with 30 mL EtOH, filtered and dried in vaccuo to afford 3.51 g as a white solid: [?]25D=−3 (c 0.94, DMSO). MS (FAB) m/z 127 (MH+).

1. filtrationwas filtered
2. concentrationconcentrated
3. customThe reaction
4. temperatureto reflux
5. additionThe addition
6. waitwas complete in ˜20 min
7. waitthe mixture had solidified after ˜40 min
8. customThe oil bath was removed
9. additionn-propanol (2×25 mL) was added
10. dissolutiondissolving the remaining sodium metal
11. customThe mixture was carefully quenched through the dropwise addition of H2O (100 mL)
12. additionSaturated aq. NaCl (20 mL) was added
13. customthe layers were separated
14. dry with materialThe organic layer was dried (MgSO4)
15. filtrationfiltered
16. additiontreated with freshly prepared MeOH/HCl
17. concentrationconcentrated
18. customThe resulting solid was triturated with 30 mL EtOH
19. filtrationfiltered
20. customdried in vaccuo
21. customto afford 3.51 g as a white solid

ORD record

ord-af7bc476414748cf9771b6c06a916f2e

Source dataset

uspto-grants-2006_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07001900B2