63126-47-6, (S)-2-(Methoxymethyl)pyrrolidine is a chiral-catalyst compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,63126-47-6
Cyanuric chloride (11.07 g, 60 mmol) was dissolved in 40 mL CH3CN and was cooled to about -20¡ã C. To this was added DIEA (11.5 mL, 60 mmol) followed by 3-fluoro-4-methoxyaninline (8.47 g, 60 mmol) in 20 mL CH3CN (reaction froze). The reaction was allowed to warm to room temperature after about 1 hour at -20¡ã C. TLC (2percent CH3OH/CH2Cl2) and mass spectroscopy indicated the presence of the compound 124. The reaction mixture was cooled to about 0¡ã C. before adding DIEA (11.5 mL, 66 mmol). 2-Aminomethyl-1-ethylpyrrolidine (7.77 g, 60 mmol) in CH3CN (10 mL) was added. The reaction was allowed to warm to rt and stirred overnight. Then DIEA (11.5 mL, 66 mmol) and S-(+)-2-methoxyethylpyrrolidine (6.91 g, 60 mmol) in 20 mL 1,4-dioxane were added. The reaction was heated at about 50¡ã C. overnight. The solvent was removed in vacuo, and the resulting residue was purified by flash chromatography on silica gel packed in ethyl acetate. The front running impurities were removed and subsequently the eluent was increased in polarity to 10percent CH3OH:ethyl acetate. The material collected from the column was then dissolved in water and extracted in CH2Cl2 (4 times), dried over MgSO4, and concentrated to dryness to give a brown solid 145 (9.7 g, 27.6percent yield), 71-72¡ã C.; HPLC: Inertsil ODS-3V C18, 40:30:30 [KH2PO4 (0.01M, pH 3.2):CH3OH:CH3CN], 264 nm, Rt 5.37 min, 90.3percent purity; 1H NMR (600 MHz, CDC3, 55¡ã C.) delta 7.69 (s, 1H), 7.08 (d, J=7.8 Hz, 1H), 6.86 (t, J=9 Hz, 1H), 4.29 (s, 1H), 3.90-3.96 (m, 1H), 3.84 (s, 3H), 3.63-3.81 (m, 6H), 3.35 (s, 3H), 3.23-3.25 (m, 1H), 2.85 (broad s, 1H), 2.78 (broad s 1H), 2.14 (broad s, 2H), 1.89-2.04 (m, 6H), 1.37 (apparent t, J=7.2 Hz, 3H); 13C NMR (150.8 MHz, CDCl3, 55¡ã C.) delta 165.8, 163.8 (2C), 152.3 (d, Jc-f=243.5 Hz), 143.0 (142.9, rotamer or diastereumer), 133.7 (133.67, rotamer or diastereomer), 115.0, 114.4, 109.1 (108.9, rotamer or diastereomer), 72.8, 66.6, 59.0, 57.0, 56.6, 53.7, 51.0, 46.8, 42.2, 28.4 (28.2, rotamer or diastereomer), 23.1 (23.0, rotamer or diastereomer), 10.9; MS (ESI) mn/z 460.2 (M+H, 44.7), 251.1 (47.7), 235.1 (27.5), 231.1 (37.4), 230.6 (100), 214.6 (36.5).
The synthetic route of 63126-47-6 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; Timmer, Richard T.; Alexander, Christopher W.; Pillarisetti, Sivaram; Saxena, Uday; Yeleswarapu, Koteswar Rao; Pal, Manojit; Reddy, Jangalgar Tirupathy; Krishma Reddy, Velagala Venkata Rama Murali; Sesila Sridevi, Bhatlapenumarthy; Kumar, Potlapally Rajender; Reddy, Gaddam Om; US2004/209882; (2004); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare