With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.39590-81-3, name is 1,1-Bis(Hydroxymethyl)cyclopropane, molecular formula is C5H10O2, molecular weight is 102.13, as common compound, the synthetic route is as follows.Formula: C5H10O2
a) [1-[5-Methyl-3-(quinolinyl-8-sulfonyloxy)phenoxy]methyl]-cyclopropylmethanol To 250 mg (0.75 mmol) of 5-methyl-3-(quinolinyl-8-sulfonyloxy)phenol, as prepared in step a of example 15, 170 mg (1.7 mmol) of 1,1-di(hydroxymethyl)cyclopropane (as prepared in US Patent 5472964), and 370 muL (1.49 mmol) of tri-n-butylphosphine in 5 mL of anhydrous tetrahydrofuran was added 378 mg (1.5 mmol) of 1,1′-(azodicarbonyl)dipiperidine. The reaction mixture was stirred at ambient temperature for 2 days. The reaction mixture was diluted with diethyl ether, filtered, and the filtrate concentrated. The residue was purified by flash chromatography (dichloromethane / ethyl acetate (2: 1 to 1: 1)) to give the title compound as a gum (177 mg. 59%). 1H-NMR (300 MHz, CDCl3) delta 9.27 (dd, 1 H, J = 2, 4 Hz), 8.42 (dd, 1 H, J = 1.5,7.5 Hz), 8.30 (dd, 1 H, J = 2, 8 Hz), 7.06 – 7.65 (m, 2 H), 6.56 (s, 1 H), 6.44 – 6.47 (m, 2 H), 3.73 (s, 2 H), 3.56 (d, 2 H, J = 5.5 Hz), 2.17 (s, 3 H), 1.79 (t, 1 H, J = 5.5 Hz), 0.53 – 0.62 (m, 4 H). Mass spectrum (MALDI-TOF, alpha-cyano-4-hydroxycinnamic acid matrix) calcd. for C21H21NO5S: 400.1 (M +H). Found: 399.8.
At the same time, in my other blogs, there are other synthetic methods of this type of compound,39590-81-3, 1,1-Bis(Hydroxymethyl)cyclopropane, and friends who are interested can also refer to it.
Reference:
Patent; Ortho-McNeil Pharmaceutical, Inc.; EP906091; (2006); B1;,
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