1) Methanesulfonylation of phthalic anhydride protected phenylglycinol

SyntheticPage 610
Published Jul 12, 2013

Reaction Scheme

Procedure

Methanesulfonyl chloride (0.32 ml, 4.12 mmol) and TEA (0.57 ml, 4.12 mmol) were added to a solution of (R)-2-(2-hydroxy-1-phenylethyl)isoindoline-1,3-dione (1.0 g, 3.7 mmol) in DCM (20 ml) and were stirred overnight. The resulting solution was washed with water (3 × 20 ml) and dried over anhydrous sodium sulphate. The solvents were removed under reduced pressure and the residue was used in the subsequent reaction without further purification. Yield 1.22 g (94%).

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2) Methanesulfonylation of BOC protected (S)-Alaninol

SyntheticPage 615
Published Jul 15, 2013

Reaction Scheme

Procedure

A solution of methanesulfonyl chloride (0.93 ml, 12 mmol) in DCM (20 ml) was added dropwise over 30 min to a solution of (S)-tert-butyl 1-hydroxypropan-2-ylcarbamate (2.0 g, 11 mmol) and TEA (1.8 ml, 12.5 mmol) in DCM (40 ml). The volatiles were then removed under reduced pressure and the residue was redissolved in ethyl acetate (30 ml) and water (30 ml). The organic layer was washed with an aqueous solution of NaHCO3 (30 ml, 5%), brine (30 ml) and dried over anhydrous Na2SO4. The product was obtained upon removal of the solvent under reduced pressure. Yield 2.1 g (75%).

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