Methyl iodide → HCID 59013445, compound

Participants

Reaction Steps

To a solution of (1S,3′R,4′S,5′R,6′R)-3′,4′,5′-tris(benzyloxy)-6′-(benzyloxymethyl)-5-chloro-6-(4-ethylbenzyl)-2,3,3′,4′,5′,6′-hexahydrospiro[indene-1,2′-pyran]-3-ol (26 mg, 0.032 mmol) in dry THF (0.8 mL) was added NaH (1.5 mg, 0.036 mmol, 60%) and CH3I (3.1 μL, 0.049 mmol) at room temperature. The reaction mixture was stirred for 3 h and quenched by addition of 5 mL of water when TLC showed the reaction was complete. Ethyl acetate (10 mL) was added to the mixture and the organic layer was separated. The aqueous layer was extracted 2× with ethyl acetate (10 mL). The combined organic layers were washed 1× with 10% HCl (10 mL), 2× with water (10 mL), 2× with brine (10 mL) prior to drying over anhydrous Na2SO4. Concentration under reduced pressure and purification of the crude product by prepared TLC provided 22 mg of the pure product.

Provenance & Evidence