5-Fluoro-2-methylbenzyl bromide → Methylamine

HRID 1822998Notes

Reaction equation

HRID 1822998 reaction equation
COC(C1CC(=O)[N:7](C2C=CC(O)=CC=2)[CH2:6]1)=O.FC1C=CC(C)=C(C=1)CBr.C[O:29][C:30]([CH:32]1[CH2:36][C:35](=[O:37])[N:34]([C:38]2[CH:43]=[CH:42][C:41]([O:44][CH2:45][C:46]3[CH:51]=[C:50]([F:52])[CH:49]=[CH:48][C:47]=3[CH3:53])=[CH:40][CH:39]=2)[CH2:33]1)=O>C(O)C>[CH3:6][NH2:7].[CH3:6][NH:7][C:30]([CH:32]1[CH2:36][C:35](=[O:37])[N:34]([C:38]2[CH:43]=[CH:42][C:41]([O:44][CH2:45][C:46]3[CH:51]=[C:50]([F:52])[CH:49]=[CH:48][C:47]=3[CH3:53])=[CH:40][CH:39]=2)[CH2:33]1)=[O:29]

Participants

6

Reactant 3

HCID 27746055-Fluoro-2-methylbenzyl bromideHCID 2883518Methyl 1-(4-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylateHCID 68614374HCID 68614374, compound

Product 2

HCID 6329MethylamineHCID 10428342HCID 10428342, compound

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 5-fluoro-2-methylbenzyl bromide giving the (RS)-1-[4-(5-fluoro-2-methyl-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid methyl ester as a white solid [71% of theory, MS: m/e=358 (M+H)+] which, thereupon, by treatment with methylamine in ethanol at 60° C. during 4 h yields the (RS)-1-[4-(5-fluoro-2-methyl-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid methylamide. Yield: 53% of theory as a colorless solid. MS: m/e=357 (M+H)+.

Sources & evidence

ORD record
ord-4cc07e29838a40d7a34eb76bdbe869ee
Source dataset
uspto-grants-2006_05
Patent number
US07037935B2

Reaction notes

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