HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 1-Tert-butoxycarbonylmethyl-3-methoxymethyl-pyrrolidine-3-carboxylic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | tert-Butyl bromoacetate | HCID 79177 | — |
| Reactant | Methyl 3-(methoxymethyl)pyrrolidine-3-carboxylate | HCID 59511362 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 1-Tert-butoxycarbonylmethyl-3-methoxymethyl-pyrrolidine-3-carboxylic acid methyl ester | HCID 59511354 | 51% |
Reaction Steps
To a stirred mixture of 3-methoxymethyl-pyrrolidine-3-carboxylic acid methyl ester (140 mg, 0.81 mmol), triethylamine (112 μl, 0.82 mmol) and cesium carbonate (263 mg, 0.81 mmol) in acetonitrile (2 ml) was added tert-butyl bromoacetate (119 μl, 0.81 mmol) slowly. The mixture was stirred for 15 minutes, filtered and concentrated. The residue was purified by column chromatography on silica gel. Elution with a solution of ethyl acetate and hexanes (1:2) provided 118 mg (51%) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08546404B2 |
| Source dataset | uspto-grants-2013_10 |
| ORD ID | ord-ca03141c2bdc44e388bf982af25ece04 |
| Source note | uspto-grants-2013_10 |