HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → HCID 10203636, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 5-Hydroxy-2-methyl-1H-indole-3-carboxylic acid benzyl ester | HCID 10923975 | — |
| Reactant | Ethyl acetate hexane | HCID 21226206 | — |
| Reactant | 1-Benzyl-3-toluenesulfonyloxypyrrolidine | HCID 86252147 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 10203636 | HCID 10203636 | 18% |
Reaction Steps
1-benzyl-3-toluenesulfonyloxypyrrolidine (0.662 g, 2.00 mmol, 1.0 eq, see Bio. Org. & Med. Chem. Lett., 1999;9:1379) was dissolved in dry acetonitrile (20 mL) and DMF (1 mL), and treated with 2-methyl-3-benzyloxycarbonyl-5-hydroxyindole (0.562 g, 2.00 mmol, 1 cq) and potassium carbonate (0.276 g, 2.0 mmol, 1.0 eq.). The reaction was heated to reflux and followed by TLC (hexane/ethyl acetate 1/1). After 24 hours, the reaction was loaded directly on silica gel and chromatographed (hexane/ethyl acetate 1/1) to afford a yellow oil: 0.162 g (18% yield). This was converted to the corresponding hydrochloride salt: LC/MS (ESI+) 441 (M+1), Anal. (C28H28N2O3.HCl.1.6H2O) C, H, N.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06951848B2 |
| Source dataset | uspto-grants-2005_10 |
| ORD ID | ord-5fb0ba0e14e54378b20f2d779a2a02fe |
| Source note | uspto-grants-2005_10 |