HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → HCID 71268665, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Ammonium Hydroxide | HCID 14923 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Reactant | Tert-butyl 6-[(benzyloxy)methyl]-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate | HCID 86677053 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | HCID 71268665 | HCID 71268665 | 76.4% |
Reaction Steps
An Et2O (25 ml) solution of tert-butyl 6-[(benzyloxy)methyl]-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate (3.37 g) was added dropwise under ice-cooling to an suspension of LAH (520 mg) in Et2O (75 ml), and was stirred at room temperature for 1 hour, Under ice-cooling, a saturated ammonia aqueous solution (1 ml) was added. After dilution with THF, stirring was performed at room temperature for 2 hours. After drying over anhydrous magnesium sulfate, Celite filtering was performed. The residue obtained by concentration was purified by silica gel column chromatography (EtOAc/hexane) to obtain tert-butyl 4-[(benzyloxy)methyl]-4-hydroxypiperidine-1-carboxylate (2.59 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08822688B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-4d4add83e12d4e4798891c3f791391bb |
| Source note | uspto-grants-2014_09 |