Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 56640794, compound

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Reaction Conditions

Reaction Steps

(+)-Camphorsulfonic acid (0.350 g, 1.51 mmol) and tetrahydrofuran (1 ml) was added to 4-[({(2S)-5-[(benzyloxy)imino]piperidin-2-yl}carbonyl)amino]piperidine-1-carboxylic acid benzyl ester (0.113 g, 0.25 mmol), and the obtained mixture was cooled down to −20° C. Borane-tetrahydrofuran complex (0.95M, 1.3 ml, 1.24 mmol) was added to the mixture, and after 9 hours of stirring, saturated sodium hydrogen carbonate aqueous solution (5 ml) was added. The reaction mixture was extracted with ethyl acetate (10 ml), and the organic layer was dried with anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain the title compound (95.3 mg) as brown oil (crude yield: 84%). The diastereo selectivity was (2S,5R)/(2S,5S)=93.2/6.8 (86.4% de).

Provenance & Evidence