HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → (2-Methylpyridin-3-yl)methanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | 2-Methylpyridine-3-carbaldehyde | HCID 11083881 | — |
| Reactant | N-[(1H-Benzo[d]imidazol-2-yl)methyl]-N-(4-(aminomethyl)-benzyl)-5,6,7,8-tetrahydroquinolin-8-amine | HCID 21985008 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (2-Methylpyridin-3-yl)methanol | HCID 302564 | 151.9% |
Reaction Steps
Using General Procedure B: To a stirred solution of 2-methyl-pyridine-3-carbaldehyde (75 mg, 0.62 mmol), N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (246 mg, 0.62 mmol) and AcOH (40 μL, 0.62 mmol) in THF (6.2 mL) was added NaBH(OAc)3 (394 mg, 1.86 mmol) and the mixture was stirred at room temperature overnight. Purification of the crude white foam (280 mg) by column chromatography on silica gel (200:3:1—CH2Cl2:MeOH:NH4OH) afforded the desired product (116 mg, 37%) as a colorless syrup.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07396840B2 |
| Source dataset | uspto-grants-2008_07 |
| ORD ID | ord-42184ea5b1004564ad09b14bdae5aea6 |
| Source note | uspto-grants-2008_07 |