HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 6-(2,4-Dichloro-benzylcarbamoyl)-2,6-diaza-spiro[3.3]heptane-2-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2,4-Dichlorobenzyl isocyanate | HCID 4612708 | — |
| Reactant | tert-Butyl 2,6-diazaspiro[3.3]heptane-2-carboxylate oxalate | HCID 53350400 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 6-(2,4-Dichloro-benzylcarbamoyl)-2,6-diaza-spiro[3.3]heptane-2-carboxylic acid tert-butyl ester | HCID 86682343 | 85.1% |
Reaction Steps
To a stirred solution of 6-(tert-butoxycarbonyl)-2,6-diaza-spiro[3.3]heptane oxalate (200 mg, 1.01 mmol) in dichloromethane (10 mL) was added triethylamine (141 μl, 1.01 mmol) followed by 2,4-dichloro-1-(isocyanatomethyl)benzene (204 mg, 1.01 mmol). The reaction mixture was stirred at ambient temperature for 1 h. The crude reaction mixture was concentrated under reduced pressure. The residue was purified by chromatography (SiO2; methanol:dichloromethane 0:1 to 1:9) to give the title compound (344 mg, 85%) as a white solid. MS (EI) m/e: 400.0 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08809552B2 |
| Source dataset | uspto-grants-2014_08 |
| ORD ID | ord-ed61985dd540493db176fb4a46aaea7f |
| Source note | uspto-grants-2014_08 |