Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylamine | HCID 674 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | HCID 10954201 | HCID 10954201 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 59497634 | HCID 59497634 | — |
Reaction Steps
To a solution of 3-Formyl-5-methyl-indolizine-1-carbonitrile (200 mg, 1.09 mmol) in CH2Cl2 (10 mL) and dimethylamine (2M MeOH solution) (1.09 mL, 2.17 mmol) was added NaBH(OAc)3 (460 mg, 2.17 mmol) at 0° C. Upon complete addition the cooling bath was removed and the reaction mixture was stirred at room temperature for 12 h. When the reaction was complete, the mixture was diluted with CH2Cl2 and washed with saturated NaHCO3. The layers were separated and the organic phase was dried over MgSO4, filtered and concentrated. The residue was purified by CombiFlash with 20% EtOAc in Hexane as the eluent to afford the desirable product 3-Dimethylaminomethyl-5-methyl-indolizine-1-carbonitrile, CAS: 3-Dimethylaminomethyl-5-methyl-indolizine-1-carbonitrile (150 mg, 65%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09150556B2 |
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| Source dataset | uspto-grants-2015_10 |
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| ORD ID | ord-0137892064c2489e862b52e06b646b41 |
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| Source note | uspto-grants-2015_10 |
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