Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | HCID 178454099 | HCID 178454099 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 178511734 | HCID 178511734 | 39.3% |
Reaction Steps
To the solution of tert-butyl(trans-3-(1H-pyrrolo[2,3-b]pyridin-1-yl)cyclobutyl)carbamate (294 mg, 1.02 mmol) in DCM (2.0 ml) was added trifluoroacetic acid, 99% (760 μl, 10.2 mmol). The reaction mixture was stirred at room temperature under N2 for 1 h. The solvent was evaporated and the residue was triturated with DCM three times, redissolved in DCM, and then treated with solid NaHCO3. The solid was filtered off and the filtrate concentrated in vacuo. The crude material was purified by chromatography through a Redi-Sep pre-packed silica gel column (12 g), eluting with a gradient of 0% to 100% EtOAc in hexane, then 15% MeOH in EtOAc, to provide trans-3-(1H-pyrrolo[2,3-b]pyridin-1-yl)cyclobutanamine (75 mg, 0.401 mmol, 39.2% yield) as light-yellow oil. ESI (M+1) 188.0.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09174992B2 |
|---|
| Source dataset | uspto-grants-2015_11 |
|---|
| ORD ID | ord-516deb8a39714743b52a3f018d74afbd |
|---|
| Source note | uspto-grants-2015_11 |
|---|