HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 3-(1-Boc-2-(r)-pyrrolidinylmethoxy)-5-(1-octynyl)pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Octyne | HCID 12370 | — |
| Reactant | 3-bromo-5-[[1-(tert-butoxycarbonyl)-2(R)-pyrrolidinyl]methoxy]pyridine | HCID 15480236 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 3-(1-Boc-2-(r)-pyrrolidinylmethoxy)-5-(1-octynyl)pyridine | HCID 22961811 | 93% |
Reaction Steps
A mixture of 3-(1-BOC-2-(R)-pyrrolidinylmethoxy)-5-bromopyridine (300 mg, 0.84 mmol), 1-octyne (0.2 mL, 1.4 mmol), Pd(PPh)3Cl2 (12 mg), CuI (catalytic amount) and NEt3 (2.45 mL) in CH2Cl2 (7 mL) was heated at reflux for 16 h. The solvent was removed, and the residue was washed with 10% NaOH then extracted with CH2Cl2. The organic extract was dried (MgSO4) and concentrated. The residue was chromatographed (silica gel; CHCl3/MeOH, 10:1) to afford the title compound (302 mg) that contaminated with starting material.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06437138B1 |
| Source dataset | uspto-grants-2002_08 |
| ORD ID | ord-7477374a8eff4573ba8db11527a307b1 |
| Source note | uspto-grants-2002_08 |