HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → HCID 77230757, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sulfuric acid magnesium salt (1:1) | HCID 24083 | — |
| Reactant | Diisobutylaluminumhydride | HCID 21225700 | — |
| Reactant | Methyl 1-(5-bromopyridin-3-yl)cyclopropanecarboxylate | HCID 59578399 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 77230757 | HCID 77230757 | — |
Reaction Steps
To a cooled (0° C.) solution of the title compound from Example 71 Step B (200 mg, 0.78 mmol) in tetrahydrofuran (3.9 mL) at 0° C. was added a solution of diisobutyl aluminum hydride in hexanes (1.0 M, 1.56 mL, 1.56 mmol). The reaction was warmed to room temperature and stirred overnight. Water and magnesium sulfate were then added, and the resulting suspension was stirred for 30 minutes, then filtered and concentrated under reduced pressure. Purification by flash chromatography on silica gel (20-100% ethyl acetate in hexanes) provided the title compound: LCMS m/z 229.67 [M+2+H]+; 1H NMR (500 MHz, CDCl3) δ 8.50 (s, 2H), 7.83 (s, 1H), 3.69 (s, 2H), 0.96-0.90 (m, 4H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09073929B2 |
| Source dataset | uspto-grants-2015_07 |
| ORD ID | ord-f6484419ed9a4fffa752cc5b487a0782 |
| Source note | uspto-grants-2015_07 |