1-(Bromomethyl)-3-(trifluoromethoxy)benzene → Methylamine

HRID 1244561Notes

Reaction equation

HRID 1244561 reaction equation
COC(C1CC(=O)[N:7](C2C=CC(O)=CC=2)[CH2:6]1)=O.FC(F)(F)OC1C=C(C=CC=1)CBr.C[O:32][C:33]([CH:35]1[CH2:39][C:38](=[O:40])[N:37]([C:41]2[CH:46]=[CH:45][C:44]([O:47][CH2:48][C:49]3[CH:54]=[CH:53][CH:52]=[C:51]([O:55][C:56]([F:59])([F:58])[F:57])[CH:50]=3)=[CH:43][CH:42]=2)[CH2:36]1)=O>C(O)C>[CH3:6][NH2:7].[CH3:6][NH:7][C:33]([CH:35]1[CH2:39][C:38](=[O:40])[N:37]([C:41]2[CH:46]=[CH:45][C:44]([O:47][CH2:48][C:49]3[CH:54]=[CH:53][CH:52]=[C:51]([O:55][C:56]([F:59])([F:58])[F:57])[CH:50]=3)=[CH:43][CH:42]=2)[CH2:36]1)=[O:32]

Participants

6

Reactant 3

HCID 7371761-(Bromomethyl)-3-(trifluoromethoxy)benzeneHCID 2883518Methyl 1-(4-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylateHCID 68614760HCID 68614760, compound

Product 2

HCID 6329MethylamineHCID 10024406HCID 10024406, 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 3-trifluoromethoxybenzyl bromide giving the (RS)-5-oxo-1-[4-(3-trifluoromethoxy-benzyloxy)-phenyl]-pyrrolidine-3-carboxylic acid methyl ester as a white solid [40% of theory, MS: m/e=410 (M+H)+] which, thereupon, by treatment with methylamine in ethanol at 80° C. yields the (RS)-5-oxo-1-[4-(3-trifluoromethoxy-benzyloxy)-phenyl]-pyrrolidine-3-carboxylic acid methylamide. Yield: 59% of theory as a white powder. MS: m/e=409 (M+H)+.

Sources & evidence

ORD record
ord-8571278a54414312888dfac4a31aea2b
Source dataset
uspto-grants-2006_10
Patent number
US07122562B2

Reaction notes

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