HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → HCID 57890363, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | 2-Methylpyrrolidine | HCID 13003 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | tert-Butyl [2-(4-formylphenyl)ethyl]carbamate | HCID 17796625 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 57890363 | HCID 57890363 | 81.1% |
Reaction Steps
To a solution of tert-butyl 2-(4-formylphenyl)ethylcarbamate (3.0 g, 12.0 mmol), 2-methylpyrrolidine (1.44 ml, 14.4 mmol) and acetic acid (1.4 ml, 24.0 mmol) in THF (100 ml) was added sodium triacetoxyborohydride (5.1 g, 24.0 mmol), and the mixture was stirred at room temperature for 16 hrs. 10% Sodium hydrogencarbonate solution (100 ml) was added to the reaction solution, and the mixture was extracted with ethyl acetate (200 ml). The extract was washed with saturated brine, and dried over magnesium sulfate, and solvent was evaporated under reduced pressure. The residue was purified by alumina column chromatography (developing solvent; hexane:ethyl acetate=4:1) to give the title compound (3.10 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07601868B2 |
| Source dataset | uspto-grants-2009_10 |
| ORD ID | ord-85454743c87f4deebc91d93834b142a2 |
| Source note | uspto-grants-2009_10 |