HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium periodate → Benzyl 4-[1-(ethoxycarbonyl)-3-oxopropyl]piperidine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium periodate | HCID 23667635 | — |
| Reactant | Ethyl 1-[(phenylmethoxy)carbonyl]-α-2-propen-1-yl-4-piperidineacetate | HCID 67441606 | — |
| Catalyst | Osmium Tetroxide | HCID 30318 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Sodium Sulfite | HCID 24437 | — |
| Solvent | Sodium Bicarbonate | HCID 516892 | — |
| Product | Benzyl 4-[1-(ethoxycarbonyl)-3-oxopropyl]piperidine-1-carboxylate | HCID 86616780 | 58.3% |
Reaction Steps
Benzyl 4-[1-(ethoxycarbonyl)but-3-en-1-yl]piperidine-1-carboxylate (4.08 g, 11.8 mmol) was dissolved in THF (45 mL), and osmium tetroxide (0.45 mL, 2.5% solution in t-butanol) was added followed by a solution of sodium periodate (7.57 g, 35.4 mmol) in water (37 mL). After 24 h, the reaction was diluted with saturated aqueous Na2SO3 and NaHCO3 and extracted with ethyl acetate (4×). The combined organic washes were dried over sodium sulfate, filtered and evaporated. The crude product was purified by silica gel chromatography, eluting with a gradient of 50 to 100% EtOAc:hexanes to give the title compound (2.39 g). MS: m/z=348.1 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07491713B2 |
| Source dataset | uspto-grants-2009_02 |
| ORD ID | ord-1ffed2019c9f4afeba41589828126113 |
| Source note | uspto-grants-2009_02 |