Ammonia → HCID 86761171, compound

Participants

Reaction Steps

At −78° C., sodium (0.28 g, 12.3 mmol) is added slowly to liquid ammonia (40 mL) followed by tris(3,5-dimethylphenyl)phosphine (2.1 g, 6.0 mmol), and the resulting mixture is stirred for 2 hours. A solution of 1-tert-butoxy-3-chloroisoquinoline (1.4 g, 6.0 mmol) in tetrahydrofuran (6 mL) is then added drop-wise and the resulting mixture slowly warmed to ambient temperature over 16 hours. The residue is quenched with water (30 mL), extracted with diethyl ether (3×25 mL), and the combined extracts are percolated through a column of magnesium sulfate-ZSM-5. The filtrate is concentrated under reduced pressure and the opaque residue is purified by a re-crystallization from methanol, yielding 1-tert-butoxy-3-(bis(3,5-dimethylphenyl)phosphino)isoquinoline (0.94 g, 73%) as a white solid.

Provenance & Evidence