HCID 77231187, compound → HCID 86651574, compound

Temperature

20 °C

To (2S,3R)-ethyl 4-benzyl-2-methyl-5-oxomorpholine-3-carboxylate (683 mg, 2.463 mmol) in THF (6 ml), BH3SMe2 (0.350 ml, 3.69 mmol) at 0° C. The reaction was stirred at 20° C. for 16 h. The reaction solution was quenched with water at 0° C. The layers were separated and the aqueous layer extracted with ethyl acetate. The combined organic layer washed with saturated NaCl. The organic was collected, dried with Na2SO4, filtered and concentrated in-vacuo to give a crude oil. The oil was purified by silica gel column chromatography (eluting with 10-20% gradient of EtOAc in hexanes using a Moritex SI-60 size 20 column). The resultant fractions were collected and concentrated in-vacuo to afford (2S,3R)-ethyl 4-benzyl-2-methylmorpholine-3-carboxylate (683 mg, 2.59 mmol, 105% yield (contained residual solvent)) as a colorless oil. MS [M+H] found 264.

1. customat 0° C
2. customThe reaction solution was quenched with water at 0° C
3. customThe layers were separated
4. extractionthe aqueous layer extracted with ethyl acetate
5. washThe combined organic layer washed with saturated NaCl
6. customThe organic was collected
7. dry with materialdried with Na2SO4
8. filtrationfiltered
9. concentrationconcentrated in-vacuo
10. customto give a crude oil
11. customThe oil was purified by silica gel column chromatography (
12. washeluting with 10-20% gradient of EtOAc in hexanes using a Moritex SI-60 size 20 column)
13. customThe resultant fractions were collected
14. concentrationconcentrated in-vacuo

ORD record

ord-574460bf904a4968a6b1ac77b733c48f

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08268819B2