HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → 4-[5-(4-Methanesulfonyl-phenyl)-2,3-dihydro-benzofuran-2-yl]-piperidine-1-carboxylic acid cyclobutyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 4-[5-(4-Methanesulfonylphenyl)-2,3-dihydrobenzofuran-2-yl]piperidine | HCID 67973289 | — |
| Reactant | Cyclobutyl-4-nitrophenyl carbonate | HCID 67973550 | — |
| Product | 4-[5-(4-Methanesulfonyl-phenyl)-2,3-dihydro-benzofuran-2-yl]-piperidine-1-carboxylic acid cyclobutyl ester | HCID 57389138 | — |
Reaction Steps
A mixture of 4-[5-(4-methanesulfonyl-phenyl)-2,3-dihydro-benzofuran-2-yl]-piperidine (100 mg), cyclobutyl-4-nitrophenyl carbonate (67 mg), and ethyldiisopropylamine (46 μL) in tetrahydrofuran (2 mL) is stirred under reflux over night. The solvent is evaporated and the residue is solved in ethyl acetate. The solution is washed with aqueous NaOH solution (1 M) and brine, dried (Na2SO4) and the solvent is evaporated to give the title compound. Yield: 92 mg (72% of theory); LC (method 2): tR=1.45 min; Mass spectrum (ESI+): m/z=456 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08669271B2 |
| Source dataset | uspto-grants-2014_03 |
| ORD ID | ord-a0221599894347b6b857f671689c0c83 |
| Source note | uspto-grants-2014_03 |