HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → 4-[2-(1-Benzyloxycarbonyl-piperidin-3-yloxy)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Diisopropyl diazene-1,2-dicarboxylate | HCID 75555 | — |
| Reactant | (S)-Benzyl 3-hydroxypiperidine-1-carboxylate | HCID 6932653 | — |
| Reactant | Tert-butyl 4-(2-hydroxyphenyl)piperazine-1-carboxylate | HCID 11543684 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-[2-(1-Benzyloxycarbonyl-piperidin-3-yloxy)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester | HCID 69423160 | 58.7% |
Reaction Steps
(S)-3-Hydroxy-piperidine-1-carboxylic acid benzyl ester (2.34 g, 8.6 mmol) was dissolved in THF (40 mL) at room temperature. 4-(2-Hydroxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (2.4 g, 8.6 mmol) and triphenylphosphine (2.7 g, 10.32 mmol) were added. Diisopropyl azodicarboxylate (2.05 mL, 10.32 mmol) was added dropwise to the solution. The reaction was stirred overnight, concentrated under reduced pressure, and purified using silica gel chromatography (100% ethyl acetate) to afford the title compound (2.5 g, 55%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07186715B2 |
| Source dataset | uspto-grants-2007_03 |
| ORD ID | ord-e9c2d97f593a4aca8996119fa259f54e |
| Source note | uspto-grants-2007_03 |