Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Reactant | HCID 90043982 | HCID 90043982 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 90043292 | HCID 90043292 | 54% |
Reaction Steps
LiAlH4 (0.35 g, 9.32 mmol) in a dried flask was cooled to 0° C., and then anhydrous THF (15 mL) was added. The mixture was stirred thoroughly and a solution of diethyl 2-((4-benzylmorpholin-3-yl)methyl)malonate (0.93 g, 2.66 mmol) in anhydrous THF (5 mL) was added, then the mixture was stirred at 70° C. for 6 hours and cooled to 30° C. To the reaction mixture were added water (0.5 mL), sodium hydroxide aqueous solution (10%, 0.5 mL) and water (3 mL) in turn, then the mixture was stirred at 25° C. for 10 minutes and filtered. The filtrate was concentrated in vacuo and the residue was purified by a silica gel column chromatography (PETROLEUM ETHER/EtOAc (V/V)=3/1) to give the title compound as colorless oil (0.38 g, 54%). The compound was characterized by the following spectroscopic data:
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09340538B2 |
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| Source dataset | uspto-grants-2016_05 |
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| ORD ID | ord-3834c29862924f60aad0deeeca2072fa |
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| Source note | uspto-grants-2016_05 |
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