(R)-3-ethynyl-3-hydroxy-1-methylpyrrolidin-2-one → HCID 86693421, compound

HRID 575374Notes

Reaction equation

HRID 575374 reaction equation
Br[C:2]1[C:21]([F:22])=[CH:20][C:5]2[O:6][CH2:7][CH:8]([OH:19])[C:9]3[S:13][C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:11][C:10]=3[C:4]=2[CH:3]=1.[C:23]([C@:25]1([OH:32])[CH2:29][CH2:28][N:27]([CH3:30])[C:26]1=[O:31])#[CH:24]>>[F:22][C:21]1[C:2]([C:24]#[C:23][C@:25]2([OH:32])[CH2:29][CH2:28][N:27]([CH3:30])[C:26]2=[O:31])=[CH:3][C:4]2[C:10]3[N:11]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[S:13][C:9]=3[CH:8]([OH:19])[CH2:7][O:6][C:5]=2[CH:20]=1

Participants

3

Reactant 2

HCID 86693296(R)-3-ethynyl-3-hydroxy-1-methylpyrrolidin-2-oneHCID 86693422HCID 86693422, compound

Product 1

HCID 86693421HCID 86693421, compound

Procedure

Ethyl 9-bromo-8-fluoro-4-hydroxy-4,5-dihydrobenzo[2,3]oxepino[4,5-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 to afford ethyl 8-fluoro-4-hydroxy-9-(((R)-3-hydroxy-1-methyl-2-oxopyrrolidin-3-yl)ethynyl)-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylate which was directed subjected to General Procedure M to afford 12.9 mg and 17.1 mg (22% overall yield) after reverse phase purification then chiral separation. The absolute stereochemistry at the 4-hydroxyl substitution position for each isomer was not determined.

Sources & evidence

ORD record
ord-a0653ffd833848e9a540383846d63561
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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