2,4,5-Trifluorobenzyl Bromide → Methylamine

HRID 1244555Notes

Reaction equation

HRID 1244555 reaction equation
COC(C1CC(=O)[N:7](C2C=CC(O)=CC=2)[CH2:6]1)=O.FC1C=C(F)C(F)=CC=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])=[CH:49][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[CH:52]=[C:51]([F:53])[C:50]([F:54])=[CH:49][C:48]=3[F:55])=[CH:41][CH:40]=2)[CH2:34]1)=[O:30]

Participants

5

Reactant 3

HCID 27770572,4,5-Trifluorobenzyl BromideHCID 2883518Methyl 1-(4-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylateHCID 68614611HCID 68614611, compound

Product 2

HCID 6329MethylamineHCID 10429718HCID 10429718, compound

Procedure

The title compound is prepared by alkylation of the (RS)-1-(4-hydroxyphenyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester with 2,4,5-trifluorobenzyl bromide giving the (RS)-5-oxo-1-[4-(2,4,5-trifluoro-benzyloxy)-phenyl]-pyrrolidine-3-carboxylic acid methyl ester as a white solid (83% of theory) which, thereupon, by treatment with methylamine yields the (RS)-5-oxo-1-[4-(2,4,5-trifluoro-benzyloxy)-phenyl]-pyrrolidine-3-carboxylic acid methylamide as a light yellow solid; MS: m/e=379 (M+H)+.

Sources & evidence

ORD record
ord-d1ea0eb547b34f418fe6a202adfd35aa
Source dataset
uspto-grants-2006_10
Patent number
US07122562B2

Reaction notes

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