HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → (3R)-3-{[(9-hydroxy-9H-fluoren-9-yl)carbonyl]oxy}-1-methyl-1-(4-oxo-4-phenylbutyl)pyrrolidinium formate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | 4-Chlorobutyrophenone | HCID 253533 | — |
| Reactant | 9-Hydroxy-9H-fluorene-9-carboxylic acid (3R)-1-methylpyrrolidin-3-yl ester | HCID 86602259 | — |
| Product | (3R)-3-{[(9-hydroxy-9H-fluoren-9-yl)carbonyl]oxy}-1-methyl-1-(4-oxo-4-phenylbutyl)pyrrolidinium formate | HCID 69480233 | 7% |
Reaction Steps
0.575 g (1.858 mmol) of 9-Hydroxy-9H-fluorene-9-carboxylic acid (3R)-1-methylpyrrolidin-3-yl ester (Intermediate I-10) and 1.018 g (5.576 mmol) of 4-chloro-1-phenylbutan-1-one in 6 ml of THF were refluxed for 20 days. After this time THF was poured off, and the residue was washed with THF in order to eliminate the alkylating agent. The product obtained (234 mg) was purified by preparative HPLC-MS to give 65 mg (7%) of the title compound (mixture of two stereoisomers) as a formate.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07192978B2 |
| Source dataset | uspto-grants-2007_03 |
| ORD ID | ord-242c962815b6439d85c4a09cc5133184 |
| Source note | uspto-grants-2007_03 |