HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzyl 3-(3-methyl-5-oxo-4,5,6,7,8,9-hexahydropyrazolo[3,4-c]isoquinolin-1-yl)-pyrrolidine-1-carboxylate → 3-Methyl-1-pyrrolidin-3-yl-3,4,6,7,8,9-hexahydropyrazolo[3,4-c]isoquinolin-5-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzyl 3-(3-methyl-5-oxo-4,5,6,7,8,9-hexahydropyrazolo[3,4-c]isoquinolin-1-yl)-pyrrolidine-1-carboxylate | HCID 136353285 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 3-Methyl-1-pyrrolidin-3-yl-3,4,6,7,8,9-hexahydropyrazolo[3,4-c]isoquinolin-5-one | HCID 135948945 | 110.2% |
Reaction Steps
A solution of EXAMPLE 24E (766 mg, 1.88 mmol) in a mixture of dichloromethane (30 mL) and methanol (30 mL) was treated with 10% palladium on carbon (150 mg) under hydrogen at ambient temperature for 6 hours. Solid material was filtered off and the filtrate concentrated to provide the title compound (564 mg, 100%). 1H NMR (DMSO-d6): 1.67-1.79 (m, 4H), 2.01-2.11 (m, 1H), 2.22-2.32 (m, 1H), 2.38-2.43 (m, 2H), 2.85-2.91 (m, 2H), 3.16-3.26 (m, 2H), 3.30 (dd, J=11.0, 8.0 Hz, 1H), 3.46 (dd, J=11.2, 7.5 Hz, 1H), 3.78 (s, 3H), 3.81-3.88 (m, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08546368B2 |
| Source dataset | uspto-grants-2013_10 |
| ORD ID | ord-a22c684307fe4da59dfc73bff01f13b3 |
| Source note | uspto-grants-2013_10 |