HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate → 1,2,3,6-Tetrahydropyridine-4-boronic acid, pinacol ester hydrochloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate | HCID 4642098 | — |
| Reactant | Hydrochloride methanol | HCID 21893726 | — |
| Product | 1,2,3,6-Tetrahydropyridine-4-boronic acid, pinacol ester hydrochloride | HCID 49761084 | 91.4% |
Reaction Steps
The mixture of tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (4.0 g, 12.9 mmol) in HCl/MeOH (20 mL) was stirred at room temperature for 1 hour. Then it was concentrated to give 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,2,3,6-tetrahydro-pyridine hydrochloride (2.9 g, 11.8 mmol, yield: 91.4%) which was used in the next step without further purification. ESI-MS (M+1): 210 calc. for C11H20BNO2 209.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08497265B2 |
| Source dataset | uspto-grants-2013_07 |
| ORD ID | ord-ad46fa4ea69e4f05b507f3fd1e657748 |
| Source note | uspto-grants-2013_07 |