HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → HCID 86659879, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | HCID 86659878 | HCID 86659878 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86659879 | HCID 86659879 | 31% |
Reaction Steps
To a solution of 1-benzyl-5-methoxy-3-methylindole (200 mg, 0.796 mmol) in a 1:1 solution (2.4 mL) of acetic acid and tetrahydrofuran was added sodium cyanoborohydride (150 mg, 2.38 mmol) at room temperature. After being stirred overnight, sodium cyanoborohydride (50 mg, 0.80 mmol) was added with additional stirring for 6 h. After the reaction mixture was neutralized by saturated NaHCO3 aqueous solution, the reaction mixture was diluted with ethyl acetate. The separated organic layer was washed with brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified with silica gel column chromatography (hexane/ethyl acetate=100/0 to 90/10) to obtain the title compound (62.4 mg, 31%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08686024B2 |
| Source dataset | uspto-grants-2014_04 |
| ORD ID | ord-ce330384a53f45d4b202e4b4a00fb0f9 |
| Source note | uspto-grants-2014_04 |