HuagongsheHuagongshe Chemistry Print Report · For research reference only
N,N,N',N'-Tetramethylethylenediamine → (1S*,2R*)-2-(1-Ethyl-1H-pyrazol-5-yl)cyclopentanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | N,N,N',N'-Tetramethylethylenediamine | HCID 8037 | — |
| Reactant | 6-Oxabicyclo[3.1.0]hexane | HCID 9244 | — |
| Reactant | 1-Ethylpyrazole | HCID 498446 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (1S*,2R*)-2-(1-Ethyl-1H-pyrazol-5-yl)cyclopentanol | HCID 89962858 | 16.3% |
Reaction Steps
The reaction and aftertreatment were conducted in the same manner as in Example 4a by using 1-ethylpyrazole (97%, 2.53 g, 25.5 mmol), N,N,N′,N′-tetramethylethylenediamine (3.83 mL, 25.5 mmol), butyl lithium (1.63 M solution in hexane; 18.3 mL, 29.8 mmol), cyclopentene oxide (2.66 g, 31.6 mmol) and THF (60 mL), to yield the title compound (750 mg, 16%) as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08889741B2 |
| Source dataset | uspto-grants-2014_11 |
| ORD ID | ord-05a9bcb18e5f4bd0ade8566e27e5e889 |
| Source note | uspto-grants-2014_11 |