HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → HCID 58495545, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Methanol | HCID 887 | — |
| Reactant | (Dimethyl sulfide)trihydroboron | HCID 12423031 | — |
| Reactant | HCID 58495633 | HCID 58495633 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 58495545 | HCID 58495545 | 36% |
Reaction Steps
Under a nitrogen atmosphere, add borane-dimethylsulfide complex (20.3 mL, 40.6 mmol, 2M solution in THF) to a solution of 5-cyclohexyloxy-pyridine-2-carbonitrile (0.82 g, 4.06 mmol) in THF (800 mL) at 0° C. Warm the mixture to room temperature and stir overnight. Cool the mixture in an ice-bath, add methanol (15 mL) and concentrated HCl (2 mL). Stir for 2 h, and concentrate in vacuo. Dissolve the residue in saturated aqueous K2CO3. Extract with DCM and wash the organic phase with water and brine. Dry the organic phase over Na2SO4, filter, and concentrate in vacuo to obtain the title compound (0.3 g, 36%). MS (ES+) m/z: 207 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08680091B2 |
| Source dataset | uspto-grants-2014_03 |
| ORD ID | ord-6bfa34e64c524aaaa7b61a50f8df82a4 |
| Source note | uspto-grants-2014_03 |