HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Hydroxide → Ammonia
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Diethyl azodicarboxylate | HCID 5462977 | — |
| Reactant | Tert-butyl 9-methyl-3,9-diazabicyclo[4.2.1]nonane-3-carboxylate | HCID 18545171 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | Ammonia | HCID 222 | — |
| Product | tert-Butyl 3,9-diazabicyclo(4.2.1)nonane-3-carboxylate | HCID 18545173 | — |
Reaction Steps
9-Methyl-3-tert-butoxycarbonyl-3,9-diazabicyclo-[4.2.1]-nonane (3.4 g, 14.1 mmol), Diethylazodicarboxylate (12.3 g, 70.7 mmol) and toluene (35 ml) was stirred at reflux for 1.5 h. Sodiumhydroxide (50 ml, 1 M) was added. The aqueous phase was extracted twice with ethyl acetate (50 ml). Chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound as an oil. Yield 1.13 g, 35%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06552012B2 |
| Source dataset | uspto-grants-2003_04 |
| ORD ID | ord-21461191bc334ca5936a130bd7cecbda |
| Source note | uspto-grants-2003_04 |