Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Sulfite | HCID 24437 | — |
| Reactant | 3,5-Bis(trifluoromethyl)styrene | HCID 2773242 | — |
| Reactant | 1-((1R)-((2R,4R,5S)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)-4-((1R)-((2R,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)phthalazine | HCID 51003674 | — |
| Solvent | tert-Butanol | HCID 6386 | — |
| Product | HCID 11161649 | HCID 11161649 | — |
Reaction Steps
3,5-Bis(trifluromethyl)styrene (13 g) was dissolved in a mixture of water (270 ml) and 2-methylpropan-2-ol (270 ml) and cooled to 0° C. AD-mix-α (76 g) was added in one portion and the reaction left to warm to room temperature over 72 hours. The mixture was then cooled to 0° C., sodium sulfite (81 g) added and the reaction mixture extracted into ethyl acetate (3×250 ml). The combined organics were dried (brine, MgSO4) and concentrated under reduced pressure to afford the product as a crude orange solid which was purified on silica eluting with 35% ethyl acetate/iso-hexane to afford the product as a crystalline white solid (chiral hplc, ee 92.2%). This was recrystallised from toluene to give the title compound as a white fibres (chiral hplc, ee 96.2%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06458830B1 |
|---|
| Source dataset | uspto-grants-2002_10 |
|---|
| ORD ID | ord-f865dd4e3b3f4f8f9b9ccf0b089f359a |
|---|
| Source note | uspto-grants-2002_10 |
|---|
