HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → 2-[2-(7-Chloro-6-nitro-2-oxo-3-thiophen-2-yl-1,2-dihydro-quinolin-4-yloxy)-ethyl]-piperidine-1-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | ethyl N-ethoxycarbonyliminocarbamate | HCID 220568 | — |
| Reactant | Tert-butyl 2-(2-hydroxyethyl)piperidine-1-carboxylate | HCID 5103438 | — |
| Reactant | 7-chloro-4-hydroxy-6-nitro-3-(thiophen-2-yl)quinolin-2(1H)-one | HCID 54711971 | — |
| Product | 2-[2-(7-Chloro-6-nitro-2-oxo-3-thiophen-2-yl-1,2-dihydro-quinolin-4-yloxy)-ethyl]-piperidine-1-carboxylic acid tert-butyl ester | HCID 53693923 | 53.2% |
Reaction Steps
To a solution of 7-chloro-4-hydroxy-6-nitro-3-thiophen-2-yl-1H-quinolin-2-one (50 mg in 2.5 mL of tetrahydrofuran) at 0° C. was added 44 mg of 2-(2-hydroxyethyl)-piperidine-1-carboxylic acid tert-butyl ester and 63 mg of triphenylphosphine followed by 0.04 mL of diethyl azodicarboxylate and the mixture warmed to room temperature. After 24 hours, the solvents were removed in vacuo and the residue purified by flash chromatography on silica gel (hexane:ethyl acetate, 90:10; then 80:20; then 60:40) to give the title compound (44 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06162813 |
| Source dataset | uspto-grants-2000_12 |
| ORD ID | ord-3631a6205f9f4aea8c9746be87505462 |
| Source note | uspto-grants-2000_12 |