1) Iodination of BOC protected phenylglycinol

SyntheticPage 612
Published Jul 15, 2013

Reaction Scheme

Procedure

(R)-tert-butyl 2-hydroxy-1-phenylethylcarbamate (1.0 g, 4.2 mmol) was dissolved in dry THF (50 ml) under argon and cooled in an ice/water bath. Imidazole (1.06 g, 15.6 mmol), triphenylphosphine (2.91 g, 11.1 mmol) and iodine (2.72 g, 10.7 mmol) were added in that order. The resulting mixure was stirred for 1 h at 0°C and then at ambient temperature for 2 d. The reaction was quenched with a saturated solution of sodium thiosulphate (40 ml) and brine (40 ml). The aqueous layer was extracted with DCM (30 ml) and the combined organic layers were dried over anhydrous magnesium suphate. The solvents were removed under reduced pressure and the residue was purified on silica using DCM as eluent. Yield 0.85 g (58%).

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2) Substitution of hydroxy by iodide in phthalic anhydride protected phenylglycinol

SyntheticPage 613
Published Jul 12, 2013

Reaction Scheme

Procedure

(R)-2-(2-hydroxy-1-phenylethyl)isoindoline-1,3-dione (1.0 g, 3.7 mmol) was dissolved in dry THF (50 ml) under argon and cooled in an ice/water bath. Imidazole (0.97 g, 14.1 mmol), triphenylphosphine (2.62 g, 10.0 mmol) and iodine (2.44 g, 9.6 mmol) were added in that order. The resulting mixure was stirred for 1 h at 0°C and then at ambient temperature for 2 d. The reaction was quenched with a saturated solution of sodium thiosulphate (40 ml) and brine (40 ml). The aqueous layer was extracted with DCM (30 ml) and the combined organic layers were dried over anhydrous magnesium sulphate. The solvents were removed under reduced pressure and the residue was purified on silica using DCM as eluent. Product used as is without further purification. Yield 0.5 g (<37%).

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