反应详情

A mixture of (2-fluoro-6-methyl-4-triisopropylsilanyloxy-phenyl)-methyl-amine (326 mg, 1.05 mmol) and 4-formyl-2-methyl-benzoic acid methyl ester (320 mg, 1.80 mmol) in 4 mL acetic acid is stirred for 2.5 hours at room temperature. Sodium triacetoxyborohydride (773 mg, 3.65 mmol) is added and stirred. Upon completion of the reaction, the mixture is concentrated and partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The aqueous layer is extracted with ethyl acetate (3×). The combined ethyl acetate layers are dried (MgSO4) and concentrated. The residue is purified on 40 g silica with ethyl acetate in heptane gradient (10% to 20%) to provide 457 mg (92%) of the titled compound as an oil. MS (ES) m/z 475.3 (M+1).

1. stirringstirred
2. customUpon completion of the reaction
3. concentrationthe mixture is concentrated
4. custompartitioned between ethyl acetate and saturated aqueous sodium bicarbonate
5. extractionThe aqueous layer is extracted with ethyl acetate (3×)
6. dry with materialThe combined ethyl acetate layers are dried (MgSO4)
7. concentrationconcentrated
8. customThe residue is purified on 40 g silica with ethyl acetate in heptane gradient (10% to 20%)