HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium triacetoxyborohydride → HCID 42629294, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | (2S)-1,2-dimethylpyrrolidine | HCID 11434918 | — |
| Reactant | 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-formyl-3-thienyl)-1H-indole-7-carboxamide | HCID 57732703 | — |
| Catalyst | Acetic Acid | HCID 176 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 42629294 | HCID 42629294 | 17.3% |
Reaction Steps
To a solution of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-formyl-3-thienyl)-1H-indole-7-carboxamide (600 mg, 1.348 mmol) in dimethyl sulfoxide (10 mL) was added of 20 drops of acetic acid and (2S)-1,2-dimethylpyrrolidine (1.37 mL, 13.483 mmol). The resulting mixture was stirred at room temperature for 6 h followed by an addition of sodium triacetoxyborohydride (2.858 g, 13.483 mmol). The reaction was stirred at room temperature overnight then purified by SFC. This compound was separated by RTP CASS Group. The fraction of enantiomer #1 is 99.7% chirally pure to give 119.9 mg of the title compound (17.3%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08063071B2 |
| Source dataset | uspto-grants-2011_11 |
| ORD ID | ord-a2f8dab1b75f4a6aaaf44b9171089ea0 |
| Source note | uspto-grants-2011_11 |