Chloroform → HCID 59371623, compound

Participants

Reaction Conditions

Reaction Steps

To a solution/suspension of 1-(3-bromophenyl)-3-phenyl-2(R)-propanol (291 mg, 1.00 mmol), 3-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]-5-(trimethylstannyl)pyridine (427 mg, 1.00 mmol, 1.00 equiv.), Pd2(dba)3.CHCl3 (15.5 mg, 15 μmol, 15 mequiv.) and CsF (304 mg, 2.00 mmol, 2.00 equiv.) in N-methylpyrrolidone (1.0 mL) contained in a dried 100 mL round-bottom flask was added P(t-Bu)3 (10 wt % in hexane, 106 μL) by syringe at room temperature under N2. The mixture was stirred for 3 h at 80° C., after which time TLC analysis indicated that the starting material had disappeared. After cooling, the reaction was quenched with saturated aqueous NH4Cl solution, and the mixture was extracted with EtOAc (3×50 mL). The organic layers were combined, washed with brine, dried over Na2SO4, and concentrated under vacuum. The residue was applied onto a silica gel column, which was eluted with EtOAc/petroleum ether/aqueous NH3 1:10:0.1-1:1:0.1 to give the product (381 mg, 80%) as a yellowish oil. 1H NMR (CDCl3, 300 MHz) δ 8.47 (s, 1H), 4.34 (s, 1H), 7.47-7.26 (m, 10H), 4.56 (m, 1H), 4.41 (m, 1H), 4.21 (dd, 1H, J=10.0, 3.0 Hz), 4.18-4.11 (m, 2H), 3.93 (t, 2H, J=6.6 Hz), 3.01-2.78 (m, 4H), 2.42-2.20 (m, 2H), 1.42 (s, 9H).

Provenance & Evidence