2,3,6-Trifluorobenzyl bromide → Methylamine

HRID 1822995Notes

Reaction equation

HRID 1822995 reaction equation
COC(C1CC(=O)[N:7](C2C=CC(O)=CC=2)[CH2:6]1)=O.FC1C(F)=CC=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[C:52]([F:53])=[CH:51][CH:50]=[C:49]([F:54])[C:48]=3[F:55])=[CH:41][CH:40]=2)[CH2:34]1)=O>>[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[C:52]([F:53])=[CH:51][CH:50]=[C:49]([F:54])[C:48]=3[F:55])=[CH:41][CH:40]=2)[CH2:34]1)=[O:30]

Participants

5

Reactant 3

HCID 5190612,3,6-Trifluorobenzyl bromideHCID 2883518Methyl 1-(4-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylateHCID 68614422(RS)-5-oxo-1-[4-(2,3,6-trifluoro-benzyloxy)-phenyl]-pyrrolidine-3-carboxylic acid methyl ester

Product 2

HCID 6329MethylamineHCID 10407290(RS)-5-oxo-1-[4-(2,3,6-trifluoro-benzyloxy)-phenyl]-pyrrolidine-3-carboxylic acid methylamide

Procedure

The title compound is prepared by alkylation of the (RS)-1-(4-hydroxyphenyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester with 2,3,6-trifluorobenzyl bromide giving the (RS)-5-oxo-1-[4-(2,3,6-trifluoro-benzyloxy)-phenyl]-pyrrolidine-3-carboxylic acid methyl ester as a light yellow solid [73% of theory, MS: m/e=379 (M+H)+], which, thereupon, by treatment with methylamine yields the (RS)-5-oxo-1-[4-(2,3,6-trifluoro-benzyloxy)-phenyl]-pyrrolidine-3-carboxylic acid methylamide.

Sources & evidence

ORD record
ord-de6e56e9e38e42f7ae84742586fd024a
Source dataset
uspto-grants-2006_05
Patent number
US07037935B2

Reaction notes

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