HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Methoxybenzoic Acid → Pyrrolidine, 1-(3-methoxybenzoyl)-
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Methoxybenzoic Acid | HCID 11461 | — |
| Reactant | Pyrrolidine | HCID 31268 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Pyrrolidine, 1-(3-methoxybenzoyl)- | HCID 786913 | 126.2% |
Reaction Steps
A solution of 3-methoxybenzoic acid (13.5 g, 88.8 mmol), pyrrolidine (9 mL, 133 mmol), HATU (33 g, 88.8 mmol) and DIEA (30 mL, 172 mmol) in DMF (100 mL) was stirred at room temperature for 2 h. The solution was added water and extracted with ethyl acetate (200 mL×3). The organic layer was dried and concentrated. The residue was purified by silica gel chromatography (eluted with petroleum ether:ethyl acetate=2:1 to 1:1) to give (3-methoxyphenyl)(pyrrolidin-1-yl)methanone (23 g, 100%) as a yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09199947B2 |
| Source dataset | uspto-grants-2015_12 |
| ORD ID | ord-12be2ae3d58f4afbbf8902a6e803dd0c |
| Source note | uspto-grants-2015_12 |