HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → (S)-3-hydroxy-1-(3-pyrrolidinophenethyl)pyrrolidine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | (r)-5,11-Dihydro-5-[1-(3-pyrrolidinophenethyl)pyrrolidin-2-ylmethyl]dibenzo[b,e][1,4]oxazepine | HCID 12990604 | — |
| Reactant | (S)-3-Hydroxypyrrolidine hydrochloride | HCID 22309122 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | (S)-3-hydroxy-1-(3-pyrrolidinophenethyl)pyrrolidine | HCID 69199429 | — |
Reaction Conditions
| Temperature | 100 °C |
|---|
Reaction Steps
3-Pyrrolidinophenethyl mesylate (1.80 g, 4.00 mmol) synthesized in Example 21, (S)-3-pyrrolidinol hydrochloride (0.50 g, 4.05 mmol) and potassium carbonate (1.70 g, 12.3 mmol) were added to acetonitrile (20 ml), and they were heated at 100° C. for 12 hours. Acetonitrile was evaporated under reduced pressure, and the residue was distributed into water and ethyl acetate. The intended product was extracted from the ethyl acetate layer with 1 M hydrochloric acid. The extract was neutralized and then the product was extracted with ethyl acetate. The organic layer was dried and the solvent was evaporated under reduced pressure to obtain (S)-3-hydroxy-1-(3-pyrrolidinophenethyl)pyrrolidine in the form of a light yellow solid (1.04 g, 100%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07320973B2 |
| Source dataset | uspto-grants-2008_01 |
| ORD ID | ord-7e676270ee5947caa3b5646c02022d38 |
| Source note | uspto-grants-2008_01 |