tert-Butyl (3R)-3-(hydroxymethyl)piperazine-1-carboxylate → tert-Butyl (3S,9aR)-3-[(3R)-3-methyl-1-oxo-3,4-dihydro-1H-isochromen-6-yl]hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate

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Reaction Steps

8G and 8H were prepared in a similar manner as 8A and 8B except (3R)-6-Bromo-3-methyl-3,4-dihydro-1H-isochromen-1-one and tert-butyl (3R)-3-(hydroxymethyl)piperazine-1-carboxylate were used as the starting materials. The cis/trans mixture was purified via chiral HPLC (20% 2:1 MeOH:MeCN/CO2) on OJ column. The slower eluting diastereomer was the trans isomer: 8G LC-MS: (M+1)+ 403; 8H: LC-MS: (M+1)+ 403.

Provenance & Evidence