Diisopropylethylamine → HCID 118093024, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 16C (2.0 g, 5.15 mmol) in CH2Cl2 (20 ml) was added TiCl4 (6.18 ml, 6.18 mmol) at 0° C. to form a yellow solution. DIEA (1.080 ml, 6.18 mmol) was added at 0° C. to form a blue solution. The mixture was stirred at 0° C. for 1 h. Benzyl chloromethyl ether (1.428 ml, 10.30 mmol) was added and stirring was continued for 2 h at 0° C. at which point the blue turn to brownish red solution. The reaction was quenched with water, diluted with EtOAc. The aqueous layer was extracted with EtOAc. The combined organic extracts were washed with sat. NaHCO3 and brine, dried over sodium sulfate and concentrated. The crude product was purified by flash chromatography (0-50% ethyl acetate/hexanes). The fractions containing the product was combined, concentrated to give 16D (2.4 g, 4.72 mmol, 92% yield) as a semi solid. 1H NMR (400 MHz, chloroform-d) δ ppm 2.41 (d, J=6.05 Hz, 3H) 2.78-2.93 (m, 1H) 3.30 (d, J=13.19 Hz, 1H) 3.43-3.57 (m, 1H) 4.01-4.23 (m, 3H) 4.46-4.81 (m, 3H) 5.36-5.53 (m, 1H) 7.01-7.16 (m, 1H) 7.18-7.41 (m, 12H).

Provenance & Evidence