HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trimethylamine → 1-benzyl-3-(BOC-amino)-3-trifluoromethylpyrrolidine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trimethylamine | HCID 1146 | — |
| Reactant | tert-Butanol | HCID 6386 | — |
| Reactant | P,P-Diphenylphosphinic azide | HCID 199401 | — |
| Reactant | 1-Benzyl-3-(trifluoromethyl)pyrrolidine-3-carboxylic acid | HCID 19691367 | — |
| Product | 1-benzyl-3-(BOC-amino)-3-trifluoromethylpyrrolidine | HCID 19691488 | 96.7% |
Reaction Steps
A mixture of 1.42 g of the compound from step 454a, 1.71 g of diphenylphosphoryl azide, 12.3 g of t-butanol and 0.627 g of trimethyl amine was heated at reflux under N2 for 24 hours. The mixture was concentrated to dryness, and the residue was dissolved in methylene chloride. The solution was washed with satd. NaHCO3 and water, then concentrated. The residue was chromatographed on silica gel to give 1.73 g of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05726182 |
| Source dataset | uspto-grants-1998_03 |
| ORD ID | ord-3c14aa7c3cf94af8afc09046f03b475b |
| Source note | uspto-grants-1998_03 |