Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 2-Methyl-2-butene | HCID 10553 | — |
| Reactant | Sodium Chlorite | HCID 23668197 | — |
| Reactant | 4-chloro-2-(7,7-dimethyl-1-oxo-1,3,4,6,7,8-hexahydro-2H-cyclopenta(4,5)pyrrolo(1,2-a)pyrazin-2-yl)nicotinaldehyde | HCID 76854078 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | tert-Butanol | HCID 6386 | — |
| Product | HCID 86684392 | HCID 86684392 | 60% |
Reaction Steps
To a mixture of 4-chloro-2-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}pyridine-3-carbaldehyde 108a (500 mg, 1.46 mmol), tert-butyl alcohol (20 mL), and dichloromethane (5 mL) was added 2-methyl-2-butene (3066 mg, 43.8 mmol). An aqueous solution (8 mL) of NaClO2 (263 mg, 2.92 mmol) and NaH2PO4.2 water (683 mg, 4.38 mmol) was added dropwise at −10° C. and the reaction mixture was stirred at −10° C. for overnight. It was concentrated under reduced pressure and the residue was extracted with ethyl acetate (4×20 mL). The combined organic extract was dried over MgSO4 and concentrated. The residue was purified with reverse-phase prep-HPLC to afford 210a (315 mg, 60%) as a pale yellow solid. MS-ESI: [M+H]+ 360.1
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09238655B2 |
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| Source dataset | uspto-grants-2016_01 |
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| ORD ID | ord-5baf455237894a7f8e5b6480becb4a11 |
|---|
| Source note | uspto-grants-2016_01 |
|---|
