Trifluoroacetic acid → (1r,2s)-2-[(Methoxycarbonyl)amino]-1-(2,5-dimethoxyphenyl)-1-propanol

関与物質

反応条件

反応手順

To a stirred solution of ketone i.e. (S)-2-[(methoxycarbonyl)amino]-1-(2,5-dimethoxyphenyl)-1-propanone (20 g, 74.9 mmol) and dimethylphenyl silane (10.7 g, 78.6 mmol) in dry DCM (500 cm3) at 0° C. in an ice bath was added dropwise trithioroacetic acid (TFA) (50 cm3). The solution was stirred at 0° C. for 1 h and then quenched by the addition of sodium hydroxide (500 cm3, 1 N). The organic layer was dried and concentrated under reduced pressure to give a yellow oil which solidified on standing. This solid was crystallized from ether/hexane to give the product as a white crystalline solid (15.6 g, 75%). 1H NMR (250 MHz; C2HCl3) 1.03 (3H, d, J7.0, CH3), 3.04 (1H, d, J4.3, OH), 3.68 (3H, s, COCH3), 3.78 (3H, s, OCH3), 3.80 (3H, s, OCH3), 3.94-3.99 (1H, m, H-2), 5.05-5.15 (2H, m, H-1 and NH), 6.72-6.85 (2H, m, ArH) 6.97 (1H, d, J 2.0, ArH).

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