Sodium borohydride → (2-(2-amino-3-morpholinoquinolin-6-yl)phenyl)(tetrahydro-2H-pyran-4-yl)methanol

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Reaction Conditions

Reaction Steps

(2-(2-Amino-3-morpholinoquinolin-6-yl)phenyl)(tetrahydro-2H-pyran-4-yl)methanone (0.164 g, 0.393 mmol, see Example 11) was dissolved in MeOH (20 mL) and treated with sodium borohydride (0.021 mL, 0.589 mmol). After 10 min, the solution was heated to 40° C. for an additional 15 minutes, then evaporated to dryness under reduced pressure. The crude material was partitioned between water (20 mL), saturated sodium bicarbonate (20 mL), and ethyl acetate (40 mL). The organic layer was dried with magnesium sulfate and evaporated to dryness under reduced pressure and the crude material was purified by silica chromatography (10-100% hexane in ethyl acetate gradient. The product peak which eluted was concentrated to give (2-(2-amino-3-morpholinoquinolin-6-yl)phenyl)(tetrahydro-2H-pyran-4-yl)methanol. MS (ESI, pos. ion) m/z: 420 (M+1).

Provenance & Evidence