Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Reactant | HCID 178444665 | HCID 178444665 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 178444662 | HCID 178444662 | 90.1% |
Reaction Steps
To a solution of 3-hexyl-6-methyl-6-[3-(4H-1,2,4-triazol-3-yl)phenyl]-3-azabicyclo[3.1.0]hexan-2-one (Preparation 43, 220 mg, 0.65 mmol) in tetrahydrofuran (5 ml) at room temperature was added lithium aluminium hydride (1.3 ml, 1.30 mmol, 1.0M in THF) dropwise over a few minutes. The mixture was then heated under reflux for 2 hours and then cooled to 0° C. 2N sodium hydroxide (1.0 ml) was added cautiously followed by ethyl acetate (10 ml) and the mixture was stirred rapidly for 30 minutes, then filtered through celite. The filtrate was concentrated in vacuo and the residue was purified by silica column chromatography eluting with ethyl acetate:methanol:amnonia solution (0.880) (80:20:1) to afford the title compound (190 mg, 90%) as a colourless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06313312B1 |
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| Source dataset | uspto-grants-2001_11 |
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| ORD ID | ord-7865d4e490c645f2ab7aa5cb26b7d5ce |
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| Source note | uspto-grants-2001_11 |
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