Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cyclohexylamine | HCID 7965 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | HCID 23435655 | HCID 23435655 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 23435659 | HCID 23435659 | 44% |
Reaction Steps
To a stirred solution of the above Compound 19b (20 mg, 0.050 mmol), cyclohexylamine (11 μL, 0.13 mmol), and BINAP (4.7 mg, 0.0075 mmol) in toluene (0.4 mL) at 25° C. was added Pd2(dba)3 (2.3 mg, 0.0025 mmol) followed by NaOtBu (12 mg, 0.13 mmol). The solution was heated to 80° C. for 15 h. The solution was cooled, poured into H2O (5 mL), extracted with EtOAc (4×5 mL), dried (MgSO4), filtered and concentrated. HPLC (gradient elution, 90-10% H2O—CH3CN) provided the title compound (9.1 mg, 0.022 mmol, 44%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06693108B2 |
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| Source dataset | uspto-grants-2004_02 |
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| ORD ID | ord-2bb80d4bed4b4e04a083f6f9d9e65d9f |
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| Source note | uspto-grants-2004_02 |
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