HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium borohydride → HCID 86759253, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | HCID 69537565 | HCID 69537565 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | HCID 86759253 | HCID 86759253 | 51.6% |
Reaction Steps
(4S,5S)-5-Hydroxy-4-isopropyl-5-trifluoromethyl-1,3-oxazolidine-3-carboxylic acid t-butyl ester (4.51 g, 0.015 mol) obtained in Example 6 was dissolved in methanol (50 ml), and thereto was slowly added sodium borohydride (500 mg, 0.013 mol) under ice-cooling, and the mixture was stirred at room temperature overnight. To the reaction solution was added saturated brine, and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=5:1) and recrystallized from n-hexane/ethyl acetate to give the desired compound (2.1 g, yield: 51%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06646150B1 |
| Source dataset | uspto-grants-2003_11 |
| ORD ID | ord-3112dd1b08af4ebca2c5f7c5ab24792e |
| Source note | uspto-grants-2003_11 |