Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Sodium borohydride | HCID 4311764 | — |
| Edukt | Dry ice ethyleneglycol | HCID 86601574 | — |
| Edukt | HCID 178476300 | HCID 178476300 | — |
| Lösungsmittel | Ethanol | HCID 702 | — |
| Produkt | HCID 178476301 | HCID 178476301 | 53% |
Reaktionsschritte
To a cooled (ethylene glycol+dry ice) solution of 2-(trans-4-(1-(tert-butoxycarbonylamino)-3-oxopropyl)cyclohexyl)ethyl acetate (1.88 g, 5.5 mmol) in ethanol (90 mL) was added NaBH4 (0.212 g, 5.5 mmol). The mixture was stirred at −10˜15° C. for 10 min and 0° C. for 10 min, and then quenched by addition of saturated aqueous NH4Cl solution (30 mL) and brine (30 mL). After removal of the volatile by evaporation, the aqueous residue was extracted with EtOAc, dried over Na2SO4. Purification by flash column chromatography (eluent: 30% EtOAc in hexanes to 40%) gave the alcohol product (1.0 g, 53%). LC/MC: 366.1 (MNa)+.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US08912169B2 |
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| Quelldatensatz | uspto-grants-2014_12 |
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| ORD ID | ord-620245cc90004280a4d74ebc9deba5ce |
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| Quellennotiz | uspto-grants-2014_12 |
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