2-(Bromomethyl)-5-(trifluoromethyl)furan → Trifluoroacetate

HRID 2261219Notes

Reaction equation

HRID 2261219 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[CH2:16][N:17]1[CH2:21][CH2:20][CH2:19][C@H:18]1[CH3:22])=[O:10].Br[CH2:24][C:25]1[O:26][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:28][CH:29]=1>>[F:31][C:30]([F:33])([F:32])[C:27]([OH:8])=[O:26].[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:24][C:25]2[O:26][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:28][CH:29]=2)[CH:5]=[CH:4][C:3]=1[C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[CH2:16][N:17]1[CH2:21][CH2:20][CH2:19][C@H:18]1[CH3:22])=[O:10].[F:31][C:30]([F:33])([F:32])[C:27]([O-:8])=[O:26]

Participants

4

Reactant 2

HCID 27946052-(Bromomethyl)-5-(trifluoromethyl)furanHCID 11960537(2-Fluoro-4-hydroxy-phenyl)-[2-(S)(2-(R)-methyl-pyrrolidin-1-ylmethyl)-pyrrolidin-1-yl]-methanone

Product 2

HCID 84468TrifluoroacetateHCID 86617870[2-Fluoro-4-(5-trifluoromethyl-furan-2-ylmethoxy)-phenyl]-[2-(s)(2-(r)-methyl-pyrrolidin-1-ylmethyl)-pyrrolidin-1-yl]-methanone trifluoroacetate salt

Procedure

The title compound is prepared in a manner substantially analogous to Procedure C from (2-Fluoro-4-hydroxy-phenyl)-[2-(S)-(2-(R)-methyl-pyrrolidin-1-ylmethyl)-pyrrolidin-1-yl]-methanone and 2-(bromomethyl)-5-(trifluoromethyl)furan [CAS 17515-77-4]. The crude product is purified by reversed phase chromatography to provide the desired product as a trifluoroacetate salt. MS (ES+) m/e 455.3

Workup

  1. customThe crude product is purified by reversed phase chromatography

Sources & evidence

ORD record
ord-605e6454da8547f988de736fce86e042
Source dataset
uspto-grants-2010_12
Patent number
US07846950B2

Reaction notes

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