Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Maleic Acid | HCID 444266 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Reactant | HCID 59134293 | HCID 59134293 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Hexane | HCID 8058 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 68429484 | HCID 68429484 | 60% |
Reaction Steps
To a solution of (7R*,8S*)-7-hydroxy-6,6-dimethyl-8-[(2-phenylethyl)amino]-4,6,7,8-tetrahydro-1,5-dioxa-4-aza-anthracene-3-one (42 mg, 0.11 mmol) in tetrahydrofuran (1.2 mL), lithium aluminum hydride (1M solution in tetrahydrofuran, 570 μL, 0.57 mmol) was added at room temperature, and the resulting mixture was stirred at 90° C. for 1.5 hour. Upon the completion of the reaction, saturated aqueous sodium hydrogencarbonate solution was added thereto, the resulting solution was extracted with ethyl acetate, washed with saturated sodium chloride solution, dried over magnesium sulfate, and concentrated. Maleic acid (13 mg, 0.11 mmol) and hexane (1 mL) were added to the solution of the resulting mixture in ethyl acetate (600 μL) at room temperature, and the resulting mixture was stirred at room temperature for 15 minutes. The resulting crystal was filtered off and the aimed product was obtained (yield: 60%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07652008B2 |
|---|
| Source dataset | uspto-grants-2010_01 |
|---|
| ORD ID | ord-befbec11689044bd8fe773742b05423a |
|---|
| Source note | uspto-grants-2010_01 |
|---|