HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethanol → 3-(4-Pentyloxy-1H-pyrazol-3-yl)-1-azabicyclo[2.2.2]octane
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | 1-Pentanol | HCID 6276 | — |
| Reactant | 3-[4-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazol-3-yl]-1-azabicyclo[2.2.2]octane | HCID 57548068 | — |
| Reactant | 3-(4-Butoxy-1H-pyrazol-3-yl)-1-azabicyclo[2.2.2]octane | HCID 178450302 | — |
| Solvent | EtOH ethyl acetate triethylamine | HCID 22328969 | — |
| Solvent | EtOH triethylamine | HCID 22663003 | — |
| Product | 3-(4-Pentyloxy-1H-pyrazol-3-yl)-1-azabicyclo[2.2.2]octane | HCID 178446977 | — |
Reaction Steps
Compound 52C was prepared following the procedure as described for the synthesis of compound 52A (see Scheme 10) using pentanol (25 ml) and 3-[4-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazol-3-yl]-1-azabicyclo[2.2.2]octane (50), (2 g, 4.61 mmol). Work-up and flash chromatography (gradient EtOH to EtOH/triethylamine 300/1) followed by a second flash chromatography (EtOH/ethyl acetate/triethylamine 25/75/1) afforded compound 51C as an oil (0.46 g, 15%). LCMS (method B); Rt: 3.30 min, ([M+H]+=394).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08735388B2 |
| Source dataset | uspto-grants-2014_05 |
| ORD ID | ord-368b0f4990d14b3890e48c8efe8318bd |
| Source note | uspto-grants-2014_05 |