Methanol → HCID 54329089, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 5-hydroxy-5-methyl-piperidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (0.08 g) and 5 mL of methanol was added 10 drops of 12 M aqueous HCl. After stirring for 1 hour, the mixture was concentrated in vacuo, and the residue was dissolved in 1 mL of DMF. After cooling to 0° C., the mixture was treated with triethylamine (0.11 mL, 0.80 mmol) and 4-benzyloxy-benzenesulfonyl chloride (0.11 g, 0.40 mmol). After stirring for 2 h at room temperature, the mixture was diluted with ethyl acetate, washed 2× with 1M HCl, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by radial chromatography (2:1 hexane-ethyl acetate, 2 mm silica gel plate) affording 0.047 g of 1-(4-benzyloxy-benzenesulfonyl)-5-hydroxy-5-methyl-piperidine-2-carboxylic acid methyl ester as a colorless solid.

Provenance & Evidence