Ethanol → HCID 86664534, compound

HRID 1910727Notes

Reaction equation

HRID 1910727 reaction equation
C(=O)(O[C@H:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]3OC(=O)[CH:15]=[C:14]([CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:12]3=2)[N:7](C(=O)C)[C@@H:6]([CH3:29])[CH2:5]1)N.[CH:31]([O-:33])=[O:32].[NH4+:34].[H][H].[CH2:37]([OH:39])[CH3:38]>[C].[Pd]>[CH2:19]([C:14]1[C:12]2=[C:13]3[C:8](=[CH:9][CH:10]=[C:11]2[O:32][C:31](=[O:33])[CH:15]=1)[N:7]([C:37](=[O:39])[CH3:38])[C@@H:6]([CH3:29])[CH2:5][C@H:4]3[NH2:34])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 2723923Ammonium formateHCID 86664532HCID 86664532, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86664534HCID 86664534, compound

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundCatalyst

Procedure

[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%).

Workup

  1. customcompletion of the reaction
  2. filtrationthe solution was filtered with celite
  3. concentrationconcentrated under reduced pressure
  4. extractionby extracting three times with chloroform
  5. washAfter washing with saturated brine
  6. concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9cf6f3e308574d0080011c06469d70a7
Source dataset
uspto-grants-2013_12
Patent number
US08604030B2

Reaction notes

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