HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acetate → HCID 58386793, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | (3R,5R)-5-((tert-Butyldimethylsilyl)oxy)piperidin-3-ol | HCID 21103800 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 58386793 | HCID 58386793 | 74% |
Reaction Steps
To a solution of (3R,5R)-5-(tert-butyldimethylsilyloxy)piperidin-3-ol (1 eq) in 20 mL of 1,4-dioxane and 8 mL of water was added benzyl chloro formate (1.5 eq). The mixture was stirred at room temperature for 4 hours. The crude mixture was diluted with 100 mL of EtOAc, washed with brine, then dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography (EtOAc:hexanes=1:3) to yield (3R,5R)-benzyl 3-(tert-butyldimethylsilyloxy)-5-hydroxypiperidine-1-carboxylate (74%). LC/MS (m/z): 366.2 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08759338B2 |
| Source dataset | uspto-grants-2014_06 |
| ORD ID | ord-4f15f5bcbc3a4fcf92b5fb71259243bf |
| Source note | uspto-grants-2014_06 |