Tris(1,1-dimethylethyl)phosphine → HCID 59807131, compound

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Reaction Steps

A suspension of Pd2(dba)3 (46 mg, 0.05 mmol) in 2 mL anhydrous THF was treated with PtBu3 (600 μL of a 10% wt in hexanes solution, 0.2 mmol) and stirred at room temperature for 5 minutes. A solution of tert-butyl 3-(6-bromo-3,4-dihydroquinolin-1(2H)-yl)pyrrolidine-1-carboxylate (381 mg, 1.00 mmol) followed by lithium hexamethyldisilizane (2.0 mL of a 1 M solution in THF, 2.0 mmol). The resulting dark brown suspension was heated at 95° C. for 1.5 hours. The mixture was cooled to room temperature and treated with 8 ml of a 1M tetrabutylammonium fluoride solution in THF then stirred at room temperature for 20 minutes. The mixture was partitioned between Et2O (100 mL) and H2O (20 mL). After extraction, the organic layer was separated and the aqueous layer was extracted once more with Et2O (50 mL). The combined organic fractions were dried over Na2SO4, filtered and concentrated to give a dark brown residue. This residue was subjected to flash chromatography on silica gel using 2.5% 2M NH3 in MeOH/CH2Cl2 to give a viscous dark brown residue (295 mg, 93.1%). 1H-NMR (CDCl3) δ 6.59-6.44 (m, 3H), 4.35-4.23 (m, 1H), 3.59-3.11 (m, 8H), 2.69 (t, J=6.3 Hz, 2H), 2.09-2.04 (m, 2H), 1.93-1.87 (m, 2H), 1.47 (s, 9H). MS (ESI): 318.2 (M+1, 100%).

Provenance & Evidence