HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Chlorophenylboronic acid → Nicotinamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Chlorophenylboronic acid | HCID 74299 | — |
| Reactant | Cyclopropanemethanol | HCID 75644 | — |
| Reactant | 3-Bromo-2-chloro-5-methylpyridine | HCID 285437 | — |
| Reactant | cis-2-Aminomethyl-1-cyclohexanol | HCID 12483365 | — |
| Product | Nicotinamide | HCID 936 | — |
Reaction Steps
The title compound was synthesized in analogy to Example 2, using 3-bromo-2-chloro-5-methyl-pyridine, hydroxymethylcyclopropane, [4-chloro-phenyl]-boronic acid and cis-2-aminomethyl-1-cyclohexanol as starting materials to yield racemic cis-5-(4-chloro-phenyl)-6-cyclopropylmethoxy-N-2-hydroxy-cyclohexylmethyl)-nicotinamide. Separation with heptane/ethanol on ChiralpakAD® yielded the (−)-enantiomer, MS (ISP) 415.2 (M+H)+, αD20: −17.8° in MeOH.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07229999B2 |
| Source dataset | uspto-grants-2007_06 |
| ORD ID | ord-ea02a304e1354ed693ad299330ccb763 |
| Source note | uspto-grants-2007_06 |