Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1-(tert-Butyl) 2-methyl (2S,4S)-4-(((4-bromophenyl)sulfonyl)oxy)pyrrolidine-1,2-dicarboxylate | HCID 56590484 | — |
| Reactant | HCID 59408876 | HCID 59408876 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | HCID 59408872 | HCID 59408872 | — |
Reaction Steps
To a solution of 8-bromo-9-methoxy-6-oxo-5,6-dihydrophenanthridine-3-carbonitrile (C1), 8-bromo-9-methoxy-6-oxo-5,6-dihydrophenanthridine-3-carbonitrile (354 mg, 1.07 mmol) in NMP (10 mL) was added 1-tert-butyl 2-methyl (2S,4S)-4-{[(4-bromophenyl)sulfonyl]oxy}pyrrolidine-1,2-dicarboxylate (549 mg, 1.18 mmol) and Cs2CO3 (876 mg, 2.69 mmol). The mixture was then heated to 60° C. for 18 h, and worked up with water and EtOAc. The organic layer was washed with brine, dried over MgSO4, and the solvent was removed in vacuo. The crude material was purified on silica (gradient elution, 10-50% EtOAc/hex) to yield the title compound. LRMS ((M-Boc)+H)+=456.2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08927569B2 |
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| Source dataset | uspto-grants-2015_01 |
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| ORD ID | ord-19f39a667e26442c936290a06fd06a26 |
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| Source note | uspto-grants-2015_01 |
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