HuagongsheHuagongshe Chemistry Print Report · For research reference only
Magnesium monoxide → 2-Oxa-4-azatetracyclo[6.3.1.16,10.01,5]tridecan-3-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Magnesium monoxide | HCID 6850729 | — |
| Reactant | 1-Adamantyl carbamate | HCID 12437646 | — |
| Reactant | 2-[2-(Carboxylatomethyl)-3-iodophenyl]acetate | HCID 21945688 | — |
| Catalyst | Acetic acid, rhodium salt (4:2) | HCID 423677 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-Oxa-4-azatetracyclo[6.3.1.16,10.01,5]tridecan-3-one | HCID 2807445 | 77% |
Reaction Steps
Tricyclo[3.3.1.13,7]dec-1-yl carbamate (100 mg, 0.512 mmol), iodobenzenediacetate (220 mg, 0.683 mmol), magnesium oxide (50 mg, 1.24 mmol) and rhodium (II) acetate dimer (22 mg, 0.050 mmol) were stirred in dichloromethane (3 mL) at 50° C. for 5 hours. After completion of the reaction, the reaction solution was filtered, and the solid was washed with chloroform and the filtrate was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1→2/1) to give the desired product (77% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08440666B2 |
| Source dataset | uspto-grants-2013_05 |
| ORD ID | ord-d4ce184fdb4f48e6b71ded0bd1b8f1ab |
| Source note | uspto-grants-2013_05 |