Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 1-(Diphenylmethyl)azetidin-3-one | HCID 3735558 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | Azetidine hydrochloride | HCID 12308726 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 57470864 | HCID 57470864 | 73.1% |
Reaction Steps
To a solution of 1-benzhydrylazetidin-3-one (750 mg) in dichloromethane (12 ml) was added azetidine hydrochloride (326 mg), followed by stirring at room temperature. Sodium triacetoxy borohydride (1.01 g) was added thereto, followed by stirring at room temperature for 25 hr. To the reaction mixture were added sodium carbonate (until bubbling stopped), water (50 ml) and ethyl acetate (100 ml). The organic layer was separated. This was washed with brine, and dried over anhydrous sodium sulfate. The organic layer after drying was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Fuji Silysia NH, eluent; heptane:ethyl acetate=1:1, 1:2, then ethyl acetate) to provide the titled compound as a pale yellow solid (643 mg, 73.1%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07855290B2 |
|---|
| Source dataset | uspto-grants-2010_12 |
|---|
| ORD ID | ord-50ed44fd4252478298515eacaffc0d6e |
|---|
| Source note | uspto-grants-2010_12 |
|---|