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With sodium tetrahydroborate; ethanol In tetrahydrofuran at 0 - 15℃;
In a dropping funnel,Thermometer dry four bottles,150 g of a compound of formula V (η = 2) was added,And 150 g of tetrahydrofuran,Stirring dissolved after cooling to 0 ~ l0 ° C,29 g of sodium borohydride was added,Further, 72 g of anhydrous ethanol was added,Insulation in the 10 ~ 15 ° C reaction to the raw material reaction is complete by adding 90g acetic acid,The pH of the reaction solution was adjusted to 4 to 5, and 330 g of water and 350 g of ethyl acetate were added thereto,The organic phase was washed with a sodium carbonate solution,Washed with a saturated saline solution,After treatment with anhydrous sodium sulfate,filter,Concentration (-0. IMPa, below 45 ° C),A solid was obtained which was beaten with 102 g of n-heptane,filter,Dried to give 111.5 g of a compound of formula IV as a white solid,The yield was 90.8percentChemical purity 96. 3percentOptical purity 99. 8percent.
With palladium 10% on activated carbon; hydrogen; In ethanol; under 760.051 Torr; for 1.5h;
Example 68A (2R)-2-Aminopentan-1,5-diol 500 mg of <strong>[478646-28-5](R)-2-Cbz-aminopentan-1,5-diol</strong> were dissolved in 250 ml of ethanol, a spatula tip of Pd/C (10%) was added and the mixture was hydrogenated with hydrogen at atmospheric pressure for 90 minutes. The reaction mixture was filtered through kieselguhr, the filter cake was washed with ethanol and the filtrate was concentrated. This gave 183 mg (78% of theory) of the target compound which was reacted further without further purification. 1H NMR (400 MHz, DMSO-d6): delta=1.00-1.15 (m, 1H), 1.30-1.65 (m, 3H), 2.55 (m, 1H; partially obscured by DMSO signal), 3.10 (dd, 1H), 3.28 (dd, 1H), 3.40 (t, 2H; partially obscured by water signal), 4.50 (br.s, 1H).
With sodium tetrahydroborate; ethanol; In tetrahydrofuran; at 0 - 15℃;
In a dropping funnel,Thermometer dry four bottles,150 g of a compound of formula V (eta = 2) was added,And 150 g of tetrahydrofuran,Stirring dissolved after cooling to 0 ~ l0 C,29 g of sodium borohydride was added,Further, 72 g of anhydrous ethanol was added,Insulation in the 10 ~ 15 C reaction to the raw material reaction is complete by adding 90g acetic acid,The pH of the reaction solution was adjusted to 4 to 5, and 330 g of water and 350 g of ethyl acetate were added thereto,The organic phase was washed with a sodium carbonate solution,Washed with a saturated saline solution,After treatment with anhydrous sodium sulfate,filter,Concentration (-0. IMPa, below 45 C),A solid was obtained which was beaten with 102 g of n-heptane,filter,Dried to give 111.5 g of a compound of formula IV as a white solid,The yield was 90.8%Chemical purity 96. 3%Optical purity 99. 8%.
With triethylamine; In dichloromethane; at -5 - 0℃;
In a dropping funnel,Thermometer in a dry three-necked flask,80 g of the compound of formula IV (n = 2)520 g of methylene chloride and adding 102.3 g of triethylamine,Stirring and cooling to -5 ~ 0 C,At this temperature, 97.6 g of methanesulfonyl chloride was added dropwise104 g of methylene chloride,After the reaction of raw materials,280 g of water was added,Heated to 15 ~ 25 C layered,The organic layer was washed with saturated brine,The organic phase was distilled under reduced pressure (below 40 C, -0.09 MPa) to give a yellow oil,Cooling to 15 ~ 20 C by adding 128g of ethanol,Cooled to -10 ~ -5 C crystallization,To obtain 107 as a white solid of formula III. 5 g,The yield was 83.1%Chemical purity 98.7%Optical purity 99. 9%.
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