Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Azetidine | HCID 10422 | — |
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | Pyrrole-3-carboxylic acid | HCID 101030 | — |
| Catalyst | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 57829664 | HCID 57829664 | 39.3% |
Reaction Steps
Oxalyl chloride (0.13 mL, 1.5 mmol) was added to a mixture of 1H-pyrrole-3-carboxylic acid (0.111 g, 1.00 mmol) and 1 drop of N,N-dimethylformamide in 5 mL of dichloromethane. The mixture was stirred for 15 h, then concentrated, then redissolved in 5 mL of dichloromethane and cooled to 0-5° C. Azetidine (0.21 mL, 2.5 mmol) was added, and the mixture was stirred for 1 h at 0-5° C. then absorbed onto silica gel and concentrated. Column chromatography (2->10% MeOH/CH2Cl2) afforded 0.059 g (39%) of azetidin-1-yl-(1H-pyrrol-3-yl)-methanone as an off-white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07939531B2 |
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| Source dataset | uspto-grants-2011_05 |
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| ORD ID | ord-dd44a7379fef4c60893bb0bb18610b9c |
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| Source note | uspto-grants-2011_05 |
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