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
Azetidine hydrochloride (326 mg) was added to a solution of 1-benzhydrylazetidin-3-one (750 mg) in dichloromethane (12 ml), followed by stirring at room temperature. Sodium triacetoxyborohydride (1.01 g) was added thereto, followed by stirring at room temperature for 25 hours. Sodium carbonate (until bubbling stopped), water (50 ml) and ethyl acetate (100 ml) was added to the reaction mixture. The organic layer was separated, washed with brine and dried over anhydrous sodium sulfate. The dried organic layer 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 give the title compound (643 mg, 73.1%) as a pale yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07790885B2 |
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| Source dataset | uspto-grants-2010_09 |
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| ORD ID | ord-e1d0c00c2cbc4a64b9d6dba696693c61 |
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| Source note | uspto-grants-2010_09 |
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