(+) -2- (difenilmetil) pirrolidin uygulaması

R) The molecular formula of - (+) -2- (diphenylmethyl) pyrrolidine is C ₁₆ H ₁₉ N, and it appears as a colorless liquid. Its molecular structure contains two benzene rings and one pyrrole structure, and it has a wide range of applications in organic synthesis.

uygulama

Dilute (R) -2- (diphenylmethyl) pyrrolidine (86.15 mg, 0.363 mmol, 1 equivalent) in 5 mL THF and cool to -78 ° C. Add n-butyl lithium dropwise (226 μ L, 0.363 mmol, 1 equivalent). The solution turned orange. After 30 minutes, add TMP-CN 6a solution dropwise to 5mL THF (60mg, 0.363mmol, 1 equivalent). Place the solution at -78 ° C for 1 hour and let it warm up to room temperature for over 2 hours. Then concentrate the deep red solution to dryness and extract with approximately 3 * 8mL of Et2O. Then concentrate these extracts again to dryness and extract with 3 * 8mL of pentane. Ligand L6 was ultimately obtained as a yellow oil and can be used in the complexation step without further purification.

At room temperature, a racemic mixture of 3-ethylbicyclo [3.2.0] hept-3-en-6-one (75.34g, 553 mmol) was added to a stirred solution of 4-pyridineformaldehyde (59.29g, 554mmol) and 4-methylmorpholine (55.9g, 553mmol) in 1-methyl-2-pyrrolidone (188mL), followed by a solution of (R) - (+) -2- (diphenylmethyl) pyrrolidine (13.11g, 55.3 mmol) in 1-ethyl-2-pyrrolidone (37.7mL). Stir the mixture at 40 ° C for 18 hours. Cool the reaction mixture to room temperature, then add 90 mL of ether. Then wash the mixture with 1M HCl (2 x 820mL), water (600mL), and saline (600mL). Separate the substrate and dry it with magnesium sulfate.

Filter the obtained solution and evaporate it under reduced pressure (200 millibars, 28 ° C) to obtain 26.4 grams of oily substance. The aqueous phase was further extracted with isohexane (200 mL), followed by washing with water (100 mL) and brine (100 mL "). The resulting solution was dried and evaporated as described above, and the residue was combined with the first batch to obtain enantiomerically enriched (1R, 5S) -3-ethylbicyclo [3.2.0] hept-3-en-6-one (28.8 g) with a yield of 38.2% and an optical purity of e. e% 96.3%.