HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diethyl Ether → Ethyl 4-(6-azaspiro(2.5)oct-6-yl)benzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diethyl Ether | HCID 3283 | — |
| Reactant | Potassium Hydroxide | HCID 14797 | — |
| Reactant | Ethyl 4-(4-methylenepiperidin-1-yl)benzoate | HCID 16109082 | — |
| Reactant | N-Methyl-N'-nitro-N-nitrosoguanidine | HCID 135436526 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Ethyl 4-(6-azaspiro(2.5)oct-6-yl)benzoate | HCID 22729977 | — |
Reaction Steps
A mixture of methyl-3-nitro-1-nitrosoguanidine (1.18 g, 8.1 mmol), 40% KOH (3.4 mL), and diethyl ether (12 mL) at 0° C. was stirred for 10 minutes. The organic phase was added slowly to a −25° C. solution of Example 158C and Pd(OAc)2 (18 mg, 0.11 mmol) in THF (8.8 mL). The mixture was stirred for 1 hour at −20° C. and concentrated. The concentrate was purified by flash column chromatography on silica gel with 9:1 hexanes/ethyl acetate to provide the desired product. MS (DCI) m/e 260 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07754886B2 |
| Source dataset | uspto-grants-2010_07 |
| ORD ID | ord-f47bac401dce46188c04fddb2d2726e3 |
| Source note | uspto-grants-2010_07 |