Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Sulfite | HCID 24437 | — |
| Reactant | Methanesulfonamide | HCID 72879 | — |
| 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 | — |
| Reactant | HCID 57889345 | HCID 57889345 | — |
| Reactant | 2-Methylpropan-2-ol--water (1/1) | HCID 71401949 | — |
| Product | HCID 57889688 | HCID 57889688 | 35.5% |
Reaction Steps
The title compound was prepared via the method of Sharpless, et. al., J. Org. Chem. 57, 1992, 2768. A stirring suspension of AD-MIX-alpha (2.3 g, 1.554 mmol) and methanesulfonamide (148 mg, 1.554 mmol) in 1:1 tert-butanol/water (16 mL) was cooled to 0° C., then treated with tert-butyl 4-(4-chlorophenyl)-5,5-dimethyl-5,6-dihydropyridine-1(2H)-carboxylate (500 mg, 1.554 mmol). The mixture was allowed to come to room temperature, and stirred for 8 days. The reaction was treated with sodium sulfite (3 g), stirred for 30 minutes, then extracted 3× with ethyl acetate. The combined organic phases were washed 3× with 1M NaOH, once with water, and once with brine, dried over sodium sulfate, and concentrated in-vacuo. The residue was purified over silica gel, eluting with ethyl acetate/hexanes (10%-20%-50% EtOAc) to yield the title compound (196 mg, 0.551 mmol, 35.5% yield) as a colorless foam. MS (ESI+)=378.26, (M+Na)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07985861B2 |
|---|
| Source dataset | uspto-grants-2011_07 |
|---|
| ORD ID | ord-c47ab6f05f3d4b288a56e0f63f773db1 |
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| Source note | uspto-grants-2011_07 |
|---|
