Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 5-Chloro-2,3-dihydro-1H-isoindol-1-one | HCID 19788108 | — |
| Reactant | HCID 86686023 | HCID 86686023 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86686024 | HCID 86686024 | 86.2% |
Reaction Steps
A mixture of 4′-bromo-5,5-dimethyl-6′,7′-dihydro-5′H-spiro[1,3-dioxane-2,8′-isoquinoline](5.0 g, 16 mmol), 5-chloro-2,3-dihydro-isoindol-1-one (2.7 g, 16 mmol), (+)-(1S,1S)-1,2-diaminocyclohexane (0.576 mL, 4.8 mmol), copper (I) iodide (456 mg, 2.4 mmol) and Cs2CO3 (10.4 g, 32 mmol) in dioxane (80 mL) was heated at 150° C. for 4 hours. After cooling to room temperature, it was diluted with water (50 mL) and extracted with EtOAc (200 mL×2). The combined organic layers were dried over anhy. Na2SO4, filtered and concentrated in vacuo to afford a crude product (5.5 g, 86%) as light yellow solid. MS: 399.1 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09133158B2 |
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| Source dataset | uspto-grants-2015_09 |
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| ORD ID | ord-3af573f4cfc54b49a24dccb1f095aeb2 |
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| Source note | uspto-grants-2015_09 |
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