HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 1-Azetidinecarboxylic acid, 2-methyl-3-oxo-, 1,1-dimethylethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | tert-butyl N-(4-diazo-3-oxobutan-2-yl)carbamate | HCID 56979712 | — |
| Catalyst | Acetic acid, rhodium(2+) salt | HCID 21674 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 1-Azetidinecarboxylic acid, 2-methyl-3-oxo-, 1,1-dimethylethyl ester | HCID 72208090 | — |
Reaction Conditions
| Temperature | 0 °C |
|---|
Reaction Steps
(3-Diazo-1-methyl-2-oxo-propyl)-carbamic acid tert-butyl ester (0.250 g, 1.17 mmol) was dissolved in anhydrous DCM (6 mL) and Et3N (1.18 mg, 0.012 mmol) was added. The reaction mixture was cooled to 0° C. and rhodium (II) acetate (0.010 g, 0.023 mmol) was added. The reaction mixture was stirred at 0° C. for 1 h then concentrated in vacuo to give 2-methyl-3-oxo-azetidine-1-carboxylic acid tert-butyl ester, which was used in the next step without further purification. TLC (eluting with 20% EtOAc/heptane) Rf=0.3.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09115151B2 |
| Source dataset | uspto-grants-2015_08 |
| ORD ID | ord-7f93eece9d644fbc8fdf13f5ad91e0fd |
| Source note | uspto-grants-2015_08 |