Hydrochloric Acid → (S)-3-[1-(2,3,6-Trichlorophenoxy)prop-2-ynyl]pyrrolidine

温度

100 °C

A mixture of (S)-3-(1-hydroxyprop-2-ynyl)pyrrolidine-1-carboxylic acid t-butyl ester (21.0 mg, 93.2 μmmol) and DIAD (22.0 μL, 112 μmmol) was dissolved in toluene (65 μL, 610 μmmol) at room temperature. PPh3 (29.3 mg, 112 μmmol) and 2,3,6-trichlorophenol (20.2 mg, 102 μmmol) were dissolved in toluene (0.1 mL, 1 mmol) and heated at 100° C. The t-butyl ester mixture was slowly added into the phenol mixture at 100° C., and stirred for 1 hour. The mixture was then removed from the heat and stirred at room temperature overnight. The mixture was then concentrated and the resulting residue was treated with 1.25M HCl in EtOH (0.6 mL, 0.8 mmol) at room temperature overnight. The mixture was concentrated and the residue was redissolved in a mixture of 50% AcOH/H2O (1.4 mL) and MeCN (0.2 mL), filtered and purified by reverse phase preparative HPLC to yield the title compound as a mono-TFA salt (21.2 mg, 99% purity). MS m/z: [M+H]+ calcd for C13H12Cl3NO, 304.00; found 304.0.

1. customThe mixture was then removed from the
2. temperatureheat
3. stirringstirred at room temperature overnight
4. concentrationThe mixture was then concentrated
5. concentrationThe mixture was concentrated
6. dissolutionthe residue was redissolved in a mixture of 50% AcOH/H2O (1.4 mL) and MeCN (0.2 mL)
7. filtrationfiltered
8. custompurified by reverse phase preparative HPLC

ORDレコード

ord-8d4c5d4177814026bd8e1e6398f39400

出典データセット

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07994209B2