Tris(1,1-dimethylethyl)phosphine → HCID 59004643, compound

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Reaction Steps

compound 102 (106 mg, 0.362 mmol), tris(dibenzylideneacetone)dipalladium (0) (33.1 mg, 0.0362 mmol) and anhydrous tetrahydrofuran (10 mL) were charged to a dry argon purged flask fitted with magnetic stir bar and condenser. A solution of tri-tert-butylphosphine (146.3 mg, 222 ul, 0.0723 mmol, 10 wt % in hexane) is added followed by dropwise addition of a 1M tetrahydrofuran solution of lithium bis(trimethylsilyl)amide (1.084 ml, 1.084 mmol) and mixture refluxed for a period of 90 minutes. The mixture was cooled to room temperature then to 0° C., quenched with 1M HCl (10 mL) and stirred for 10 minutes. The solution was diluted with ethyl acetate and 5M NH4OH added to adjust pH to 9. The mixture was transferred to a separatory funnel and the organic layer collected. The aqueous layer was further extracted with ethyl acetate and the combined organic layers were washed with brine, dried over magnesium sulphate, filtered, concentrated and the residue purified via chromatography on silica gel (MeOH:CH2Cl2, 1:9) to yield compound 103 (67 mg, 80.8%)as a pale yellow solid. 1H NMR (DMSO-d6) δ 1.40-1.70 (2×m, 4H), 2.08-2.20 (m, 1H), 2.18 (s, 3H), 2.89-2.99 (m, 1H), 3.89 (dd, 1H, J=14.1, 6.9 Hz), 4.12 (dd, 1H, J=14.2, 5.1 Hz), 4.46 (brs, 2H), 6.10 (d, 1H, J=3.0 Hz), 6.51 (dd, 1H, J=8.7, 2.0 Hz), 6.66 (d, 1H, J=2.0 Hz), 7.12-7.15 (m, 2H); ESI-MS (m/z, %): 230 (MH+, 100%).

Provenance & Evidence