Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | Pyrrolidine | HCID 31268 | — |
| Reactant | HCID 67585497 | HCID 67585497 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Product | HCID 67584924 | HCID 67584924 | — |
Reaction Steps
To a solution of 0.666 g (1.665 mmol) of (Z)-5-(3-chlorostilbene-4'-sulfonyl)-4,5,6,7-tetrahydrofuro[3,2-c]pyridin in 10 ml of acetic acid, 0.21 ml (2.5 mmol) of pyrrolidine and 0.20 g (2.5 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 1 hour. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with aqueous sodium hydroxide and extracted with ethyl acetate 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=4/1) to yield the desired product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05998433 |
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| Source dataset | uspto-grants-1999_12 |
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| ORD ID | ord-9e739f2d255c4486873a3a66101fba96 |
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| Source note | uspto-grants-1999_12 |
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