HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Prolinol, (R)- → 5-(5-{[(2R)-2-(hydroxymethyl)-1-pyrrolidinyl]methyl}-3-thienyl)-3-{1-[(1-methylethyl)sulfonyl]-4-piperidinyl}-1H-indole-7-carboxamide
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Prolinol, (R)- | HCID 2724541 | — |
| Edukt | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Edukt | 5-(5-formyl-3-thienyl)-3-{1-[(1-methylethyl)sulfonyl]-4-piperidinyl}-1H-indole-7-carboxamide | HCID 57732783 | — |
| Katalysator | Acetic Acid | HCID 176 | — |
| Lösungsmittel | Dimethyl Sulfoxide | HCID 679 | — |
| Produkt | 5-(5-{[(2R)-2-(hydroxymethyl)-1-pyrrolidinyl]methyl}-3-thienyl)-3-{1-[(1-methylethyl)sulfonyl]-4-piperidinyl}-1H-indole-7-carboxamide | HCID 57732666 | 69,7% |
Reaktionsschritte
To a solution of 5-(5-formyl-3-thienyl)-3-{1-[(1-methylethyl)sulfonyl]-4-piperidinyl}-1H-indole-7-carboxamide (25 mg, 0.054 mmol) in DMSO (2 mL) was added (2R)-2-pyrrolidinylmethanol (101.15 mg, 1 mmol) and 2 drops of acetic acid. The resulting mixture was stirred at room temperature for 4 h followed by an addition of sodium triacetoxyborohydride (212 mg, 0.54 mmol). The mixture was reacted overnight. It was then purified by Gilson Preparatory HPLC to give 20.5 mg of the title compound (69.7%).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08354406B2 |
| Quelldatensatz | uspto-grants-2013_01 |
| ORD ID | ord-02bc6af579b5458f9e3061480e327534 |
| Quellennotiz | uspto-grants-2013_01 |