Trifluoroacetic acid → Trifluoroacetic acid

HRID 2209029Notes

Reaction equation

HRID 2209029 reaction equation
BrC1N=C([O:8][C@@H:9]([C@H:11]2[CH2:15][N:14]([C@@H:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[CH3:17])[C:13](=[O:26])[CH2:12]2)[CH3:10])C2N(C)C=NC=2C=1.[C:31]([OH:37])([C:33]([F:36])([F:35])[F:34])=[O:32]>>[OH:8][C@@H:9]([C@H:11]1[CH2:15][N:14]([C@@H:16]([C:18]2[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=2)[CH3:17])[C:13](=[O:26])[CH2:12]1)[CH3:10].[C:31]([OH:37])([C:33]([F:36])([F:35])[F:34])=[O:32]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117842978(R)-4-((R)-1-(6-bromo-3-methyl-3H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)-1-((R)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one

Product 2

HCID 6422Trifluoroacetic acidHCID 117843967(R)-4-((R)-1-hydroxyethyl)-1-((R)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one

Procedure

A solution of (R)-4-((R)-1-(6-bromo-3-methyl-3H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)-1-((R)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one 2.61 (256 mg, 0.54 mmol) in TFA (8 mL) was heated at 55° C. for 16 h, cooled to rt and then evaporated to give (R)-4-((R)-1-hydroxyethyl)-1-((R)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one 2.62 as TFA salt, which was used without purification.

Workup

  1. customevaporated

Sources & evidence

ORD record
ord-d220227785cc411a9843685d10202af3
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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