(R)-3-ethynyl-3-hydroxy-1-methylpyrrolidin-2-one → HCID 86693410, compound

Participants

Reaction Steps

Methyl 9-bromo-4-hydroxy-4,5-dihydro-[1]benzoxepino[5,4-d]thiazole-2-carboxylate was reacted similarly to as described in General Procedure P with non-critical modifications to afford 142 mg (94%) of methyl 9-bromo-4-fluoro-4,5-dihydro-[1]benzoxepino[5,4-d]thiazole-2-carboxylate. Methyl 9-bromo-4-fluoro-4,5-dihydro-[1]benzoxepino[5,4-d]thiazole-2-carboxylate was reacted with (3R)-3-ethynyl-3-hydroxy-1-methyl-pyrrolidin-2-one similarly to as described in General Procedure F with non-critical modifications to afford methyl 4-fluoro-9-[2-[(3R)-3-hydroxy-1-methyl-2-oxo-pyrrolidin-3-yl]ethynyl]-4,5-dihydro-[1]benzoxepin o[5,4-d]thiazole-2-carboxylate which was directed subjected to General Procedure M to afford 29 mg and 30 mg (37% overall yield) after reverse phase purification then chiral separation. The absolute stereochemistry at the 4-fluorine substitution position for each isomer was not determined.

Provenance & Evidence