Sodium Hydroxide → HCID 118006716, compound

To a stirred solution of (2R,6R)-6-((benzyloxy)methyl)-2-ethylmorpholin-3-one (362.2 mg, 1.453 mmol) in THF (2 mL) was added 1 M lithium tetrahydroaluminate in THF (2 mL, 2 mmol) dropwise at rt over a 2-min period. The reaction was stirred at rt for 2.5 h after which time it was cooled to 0° C. followed by a dropwise addition of water (0.6 mL) and then 1 M sodium hydroxide in water (0.04 mL). The quenched reaction was warmed to rt, stirred until a granular solid was formed and filtered over a Celite 545 pad rinsing with EtOAc (5 mL), DCM (5 mL) and ethyl ether (5 mL). The filtrate was concentrated and the resultant crude product was purified over silica gel (Biotage, eluting with a gradient of 5-10% MeOH in DCM) followed by combining the desired fractions, concentration and drying in vacuo to provide (2R,6R)-2-((benzyloxy)methyl)-6-ethylmorpholine (50.2 mg, 0.213 mmol, 14.6% yield).

1. temperaturewas cooled to 0° C.
2. customThe quenched reaction
3. temperaturewas warmed to rt
4. stirringstirred until a granular solid
5. customwas formed
6. filtrationfiltered over a Celite 545 pad
7. washrinsing with EtOAc (5 mL), DCM (5 mL) and ethyl ether (5 mL)
8. concentrationThe filtrate was concentrated
9. customthe resultant crude product was purified over silica gel (Biotage
10. washeluting with a gradient of 5-10% MeOH in DCM)
11. concentrationfractions, concentration
12. customdrying in vacuo

ORD record

ord-ed46038b69aa482893f14cc4e37c3d3b

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428495B2