Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Dimethylacetamide | HCID 31374 | — |
| Reactant | 2-(Di-tert-butylphosphino)biphenyl | HCID 2734215 | — |
| Reactant | HCID 86643135 | HCID 86643135 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | Zinc | HCID 23994 | — |
| Catalyst | Allyl(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)chloropalladium(II) | HCID 105144 | — |
| Product | HCID 68250502 | HCID 68250502 | — |
Reaction Steps
Tert-butyl (1S)-1-phenyl-8-{[(trifluoromethyl)sulfonyl]oxy}-3,4-dihydroisoquinoline-2(1H)-carboxylate (3.75 g) was dissolved in N,N-dimethylacetamide (40 mL). To the reaction mixture were added zinc (537 mg), zinc cyanide (1.15 g), trifluoroacetic palladium (II) (682 mg), and biphenyl-2-yl(di-tert-butyl)phosphine (1.22 g). The temperature was increased from room temperature to 95° C. over 45 minutes and then the mixture was stirred at 95° C. for 18 hours. Water was added to the mixture which was then filtered through celite. Thereafter, the mixture was extracted with diethyl ether. The extract was washed with a saturated aqueous sodium chloride solution, and then dried over magnesium sulfate. The solvent was evaporated and the resulting residue was purified by silica gel column chromatography (EtOAc:hexane) to obtain tert-butyl (1S)-8-cyano-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate (796 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08263607B2 |
|---|
| Source dataset | uspto-grants-2012_09 |
|---|
| ORD ID | ord-02bd3fb2443a44329eb9e384814ab3cd |
|---|
| Source note | uspto-grants-2012_09 |
|---|
