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2,4,6-Trifluorobenzyl bromide → Methylamine

HRID 1244558
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Reaction equation

HRID 1244558 reaction equation
COC(C1CC(=O)[N:7](C2C=CC(O)=CC=2)[CH2:6]1)=O.FC1C=C(F)C=C(F)C=1CBr.C[O:30][C:31]([CH:33]1[CH2:37][C:36](=[O:38])[N:35]([C:39]2[CH:44]=[CH:43][C:42]([O:45][CH2:46][C:47]3[CH:52]=[C:51]([F:53])[C:50]([F:54])=[C:49]([F:55])[CH:48]=3)=[CH:41][CH:40]=2)[CH2:34]1)=O>C(O)C>[CH3:6][NH2:7].[CH3:6][NH:7][C:31]([CH:33]1[CH2:37][C:36](=[O:38])[N:35]([C:39]2[CH:44]=[CH:43][C:42]([O:45][CH2:46][C:47]3[CH:52]=[C:51]([F:53])[C:50]([F:54])=[C:49]([F:55])[CH:48]=3)=[CH:41][CH:40]=2)[CH2:34]1)=[O:30]
ParticipantsProcedureSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 27770592,4,6-Trifluorobenzyl bromideHCID 2883518Methyl 1-(4-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylateHCID 68615462(RS)-5-oxo-1-[4-(3,4,5-trifluoro-benzyloxy)-phenyl]-pyrrolidine-3-carboxylic acid methyl ester

Product 2

HCID 6329MethylamineHCID 10384975(RS)-5-oxo-1-[4-(3,4,5-trifluoro-benzyloxy)-phenyl]-pyrrolidine-3-carboxylic acid methylamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound is prepared by alkylation of the (RS)-1-(4-hydroxyphenyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester with 2,4,6-trifluorobenzyl bromide giving the (RS)-5-oxo-1-[4-(3,4,5-trifluoro-benzyloxy)-phenyl]-pyrrolidine-3-carboxylic acid methyl ester as a white solid (99% of theory) which, thereupon, by treatment with methylamine in ethanol at 50° C. yields the (RS)-5-oxo-1-[4-(3,4,5-trifluoro-benzyloxy)-phenyl]-pyrrolidine-3-carboxylic acid methylamide. Yield: 99% of theory as a white solid; MS: m/e=379 (M+H)+.

Sources & evidence

ORD record
ord-9e4fe24ebd284e9990a7cbff83af1d54
Source dataset
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07122562B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes