HuagongsheHuagongshe Chemistry Print Report · For research reference only
5-Fluoro-2-methylbenzyl bromide → Methylamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 5-Fluoro-2-methylbenzyl bromide | HCID 2774605 | — |
| Reactant | Methyl 1-(4-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylate | HCID 2883518 | — |
| Reactant | (RS)-1-[4-(5-fluoro-2-methyl-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid methyl ester | HCID 68614374 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | Methylamine | HCID 6329 | — |
| Product | HCID 10428342 | HCID 10428342 | — |
Reaction Steps
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)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07122562B2 |
| Source dataset | uspto-grants-2006_10 |
| ORD ID | ord-84d33926a2ea4defad22f30f0d2215ed |
| Source note | uspto-grants-2006_10 |