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A solution of 2-(6-hydroxy-2,3-dihydrobenzofuran-3-yl)acetic acid (1.1 g, 5.7 mmol) in methanol (20 mL), was added dropwise with thionyl chloride (0.67 g, 5.7 mmol) under ice-cooling, and the addition was complete in 10 minutes. Followed by stirring at room temperature for 2 hours. The solvent was removed by rotary evaporation and added toluene to remove the excess of thionyl chloride, the product was obtained as a brown solid (1.1 g, 93percent yield).
[(3R)-6-hydroxy-2,3-dihydro-1-benzofuran-3-yl]acetic acid (S)-2-amino-1,1-diphenylpropan-1-ol salt[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With hydrogen;dichloro [(+)-1,2-bis((2R,5R)-2,5-diisopropylphosphorano)benzene]ruthenium (II)-N,N-dimethylformamide complex; In methanol; at 20℃; for 12h;
Example 38Synthesis of [ (3S) -6-hydroxy-2, 3-dihydro-l-benzofuran-3- yl] acetic acid (S) -2-amino-l, 1-diphenylpropan-l-ol salt; A racemate (0.05 g) of (6-hydroxy-2, 3-dihydro-l- benzofuran-3-yl) acetic acid was charged, a mixed solvent of methanol/isopropyl alcohol (1/4) was added, and the racemate was dissolved. (S) -2-Amino-l, 1-diphenylpropan-l-ol (0.059 g, 1 eq) was added thereto, and the mixture was stirred at room temperature for 12 hr. The precipitated crystals werecollected by filtration to give the title compound (0.037 g) . 87.8%de(high performance liquid chromatography conditions)column: CHIRALPAK AD-H (manufactured by DAICEL CHEMICALINDUSTRIES, LTD.)mobile phase: normal hexane/ethanol/trifluoroacetic acid(volume ratio: 90/10/0.1)flow rate: 1.0 mL/mindetection: UV 220 nmtemperature: 25C
With palladium on activated charcoal; hydrogen; In acetic acid; at 40℃; for 24h;
<strong>[69716-04-7]2-<strong>[69716-04-7](6-hydroxybenzofuran-3-yl)acetic acid</strong></strong> (1.2 g, 6.3 mmol) was added to HOAc (20 mL), Pd / C (0.12 g) was added and the reaction was carried out with hydrogen at 40 C for 24 hours. Celite vacuum filtration, the filter cake was washed with methanol, the filtrate was evaporated in vacuo to give the product as a white solid (1.1 g, 90% yield).
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