Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Lithium borohydride | HCID 4148881 | — |
| Reactant | HCID 86601259 | HCID 86601259 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86601258 | HCID 86601258 | 44.8% |
Reaction Steps
Dissolve [5-[1-(3,5-bis-trifluoromethyl-benzyl)-5-dimethylamino-1H-[1,2,3]triazol-4-yl]-4-(2-chloro-4-fluoro-benzyl)-4H-[1,2,4]triazol-3-yl]-acetic acid ethyl ester (338 mg) in THF (5 mL). Cool to 0° C., add 2M LiBH4 (0.8 mL, 2M soln in THF) and stir overnight while slowly warming to RT. Pour reaction into aqueous NH4Cl (15 mL) and extract with EtOAc (2×15 mL). Purify via radial chromatography using a gradient of 1:1 to 1:5 hexanes:EtOAc to give the title compound (137 mg, 44%). MS (IS) 592.0 (M+1); Rf=0.11 (1:5 hexanes:EtOAc).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07320994B2 |
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| Source dataset | uspto-grants-2008_01 |
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| ORD ID | ord-b3d9ed28fbda4fef8092b548dccbc821 |
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| Source note | uspto-grants-2008_01 |
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