1-(Bromomethyl)-2-methoxybenzene → Methylamine

HRID 1244560Notes

Reaction equation

HRID 1244560 reaction equation
COC(C1CC(=O)[N:7](C2C=CC(O)=CC=2)[CH2:6]1)=O.COC1C=CC=CC=1CBr.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]=[CH:50][CH:49]=[CH:48][C:47]=3[O:52][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]=[CH:50][CH:49]=[CH:48][C:47]=3[O:52][CH3:53])=[CH:40][CH:39]=2)[CH2:33]1)=[O:29]

Participants

6

Reactant 3

HCID 403081-(Bromomethyl)-2-methoxybenzeneHCID 2883518Methyl 1-(4-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylateHCID 68614923HCID 68614923, compound

Product 2

HCID 6329MethylamineHCID 10383487HCID 10383487, 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 2-methoxybenzylbromide giving the (RS)-1-[4-(2-methoxy-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid methyl ester as a light yellow oil [83% of theory, MS:m/e=355 (M+H)+ which, thereupon, by treatment with methylamine in ethanol at 80° C. yields the (RS)-1-[4-(2-methoxybenzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid methylamide. Yield: 47% of theory as a white solid. MS: m/e=355 (M+H)+.

Sources & evidence

ORD record
ord-76c5059278ea4582810e7dcd1ec1a5c2
Source dataset
uspto-grants-2006_10
Patent number
US07122562B2

Reaction notes

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