HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl iodide → Tert-butyl 3-(3-chloro-4-fluorophenyl)-3-methoxypyrrolidin-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Tert-butyl 3-(3-chloro-4-fluorophenyl)-3-hydroxypyrrolidine-1-carboxylate | HCID 67402987 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Tert-butyl 3-(3-chloro-4-fluorophenyl)-3-methoxypyrrolidin-1-carboxylate | HCID 67402089 | 56% |
Reaction Steps
Preparation according to Preparation 2. Tert-butyl-3-(3-chloro-4-fluorophenyl)-3-hydroxypyrrolidin-1-carboxylate (3.1 g, 9.84 mmol) in dry tetrahydrofuran (50 mL), sodium hydride (60% dispersion in mineral oil, 0.59 g, 14.76 mmol), iodomethane (1.22 mL, 19.68 mmol). Purification by flash column chromatography on silica gel (ethyl acetate/isooctane, 1:9 to 1:1) gave the title compound (1.81 g, 56%). MS m/z (rel. intensity, 70 eV) 273 (19), 228 (13), 187 (17), 133 (12), 57 (bp).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09035073B2 |
| Source dataset | uspto-grants-2015_05 |
| ORD ID | ord-0b378efeb21745819966707fd09908d0 |
| Source note | uspto-grants-2015_05 |