HCID 86592849, compound → HCID 69652392, compound

HRID 2212211Notes

Reaction equation

HRID 2212211 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]([N:14]2[C:23]3[CH:22]=[CH:21][CH:20]=[C:19]([Cl:24])[C:18]=3[C:17]3=[N:25][O:26][C:27]([CH3:28])=[C:16]3[C:15]2=[O:29])[CH2:11][CH:10]([CH2:30][N:31]=[N+]=[N-])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1.CCO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]([N:14]2[C:23]3[CH:22]=[CH:21][CH:20]=[C:19]([Cl:24])[C:18]=3[C:17]3=[N:25][O:26][C:27]([CH3:28])=[C:16]3[C:15]2=[O:29])[CH2:11][CH:10]([CH2:30][NH2:31])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 1

HCID 86592849HCID 86592849, compound

Product 1

HCID 69652392HCID 69652392, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Hydrogenate 3-azidomethyl-5-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-piperidine-1-carboxylic acid tert-butyl ester (0.65 g, 1.4 mmol) in THF (7.5 mL) and EtOH (50 mL) with 5% Pd/C (0.132 g, at 50 psi and room temperature for 24 H. Filter through celite and concentrate to dryness. Dissolve in CHCl3. Wash 2× with sat. aq NaHCO3, wash with brine, dry over Na2SO4, filter and concentrate to dryness to afford the title compound (413 mg, 66%) as a tan foam as a mixture of cis isomers. MS(IS) 447.1 (M+); TLC (10% MeOH/CHCl3) Rf=0.14.

Workup

  1. customat 50 psi and room temperature
  2. filtrationFilter through celite
  3. concentrationconcentrate to dryness
  4. dissolutionDissolve in CHCl3
  5. washWash 2× with sat. aq NaHCO3
  6. washwash with brine
  7. dry with materialdry over Na2SO4
  8. filtrationfilter
  9. concentrationconcentrate to dryness

Sources & evidence

ORD record
ord-19d310b3307d406e878e7e1fdb83b1b3
Source dataset
uspto-grants-2006_09
Patent number
US07101891B2

Reaction notes

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