(R)-3-ethynyl-3-hydroxy-1-methylpyrrolidin-2-one → HCID 86693417, compound

Participants

Reaction Steps

Ethyl 9-bromo-8-fluoro-4-hydroxy-4-methyl-5H-[1]benzoxepino[5,4-d]thiazole-2-carboxylate (170 mg) was reacted similarly to as described in General Procedure P with non-critical modifications to afford 130 mg (76%) of ethyl 9-bromo-4,8-difluoro-4-methyl-5H-[1]benzoxepino[5,4-d]thiazole-2-carboxylate. Ethyl 9-bromo-4,8-difluoro-4-methyl-5H-[1]benzoxepino[5,4-d]thiazole-2-carboxylate (122 mg) 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 ethyl 4,8-difluoro-9-[2-[(3R)-3-hydroxy-1-methyl-2-oxo-pyrrolidin-3-yl]ethynyl]-4-methyl-5H-[1]benzoxepino[5,4-d]thiazole-2-carboxylate which was directed subjected to General Procedure M to afford 7.2 mg and 6.9 mg (11% 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