HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → HCID 86713334, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | tert-Butyl 3-{[(benzyloxy)(hydroxy)methylidene]amino}pyrrolidine-1-carboxylate | HCID 12184171 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86713334 | HCID 86713334 | 91.9% |
Reaction Steps
Sodium hydride (60% oil dispersion, 0.32 g) was added to a stirred solution of tert-butyl (S)-3-benzyloxycarbonylaminopyrrolidine-1-carboxylate (prepared according to Cheng et al, WO2007 142585, 1.73 g) in THF (20 mL) and the mixture was stirred for 15 minutes. Iodomethane (1.85 g) was added and the mixture was stirred at room temperature for 1 hour. Methanol was carefully added to destroy the excess sodium hydride then ethyl acetate and water were added and the organic layer was washed with brine, dried (Na2SO4), filtered. The filtrate was concentrated in vacuo to give tert-butyl (S)-3-(N-benzyloxycarbonyl-N-methylamino)pyrrolidine-1-carboxylate (1.66 g) as a pale coloured oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09290472B2 |
| Source dataset | uspto-grants-2016_03 |
| ORD ID | ord-4ddb955915904e899aa09e807c6de1f7 |
| Source note | uspto-grants-2016_03 |