Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Ammonium formate | HCID 2723923 | — |
| Reactant | HCID 86664532 | HCID 86664532 | — |
| Reactant | HCID 178418361 | HCID 178418361 | — |
| Catalyst | HCID 178418390 | HCID 178418390 | — |
| Product | HCID 86664534 | HCID 86664534 | — |
Reaction Steps
[Step 4] 170 mg of the cis-benzyl-7-acetyl-8-methyl-3-oxo-7,8,9,10-tetrahydro-3H-pyrano[3,2-f]-quinolin-10-yl carbamate and 132 mg of ammonium formate were dissolved in 5 mL of ethanol followed by adding 51 mg of 10% palladium carbon and stirring for 7.5 hours in a hydrogen atmosphere at normal pressure and room temperature. Following completion of the reaction, the solution was filtered with celite and then concentrated under reduced pressure. The resulting residue was neutralized with saturated aqueous sodium bicarbonate solution followed by extracting three times with chloroform. After washing with saturated brine and dehydrating with anhydrous sodium sulfate, the solution was concentrated under reduced pressure to obtain 23 mg of cis-benzyl-7-acetyl-10-amino-8-methyl-7,8,9,10-tetrahydro-3H-pyrano[3,2-f]-quinolin-3-one in the form of a colorless oil (20%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08604030B2 |
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| Source dataset | uspto-grants-2013_12 |
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| ORD ID | ord-9cf6f3e308574d0080011c06469d70a7 |
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| Source note | uspto-grants-2013_12 |
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