反应详情

To a stirred solution of the above 2-amino-1-morpholin-4-yl-ethanone hydrochloride (0.23 g, 1.3 mmol) in methylene chloride (4.0 mL) and triethylamine (0.19 mL, 1.4 mmol), 4 angstrom sieves (10 beads, pulverized to a powder) were added, followed by trimethylacetaldehyde (0.35 mL, 3.3 mmol) at room temperature, under argon. The resulting mixture was stirred at room temperature overnight after which time sodium triacetoxyborohydride (0.54 g, 2.6 mmol) was added. After 6 h, the solids were removed via filtration and washed with methylene chloride. The combined filtrates were concentrated and the remaining residue was diluted with EtOAc and water. The aqueous phase was lyophilized to give a white solid that was diluted with EtOAc. The solids were removed via filtration and washed with EtOAc. The combined organics were concentrated to give the crude product which was purified via silica gel flash chromatography eluting with 100% EtOAc, then 0.5% NH4OH/10% MeOH/EtOAc, flow rate 30 mL/min. The product-containing fractions were concentrated to give 0.18 g (67%) of 2-(2,2-dimethyl-propylamino)-1-morpholin-4yl-ethanone.

1. additionwere added
2. additionwas added
3. customthe solids were removed via filtration
4. washwashed with methylene chloride
5. concentrationThe combined filtrates were concentrated
6. additionthe remaining residue was diluted with EtOAc and water
7. customto give a white solid
8. customThe solids were removed via filtration
9. washwashed with EtOAc
10. concentrationThe combined organics were concentrated
11. customto give the crude product which
12. customwas purified via silica gel flash chromatography
13. washeluting with 100% EtOAc
14. concentrationThe product-containing fractions were concentrated