Sodium Bicarbonate → HCID 59398062, compound

HRID 2193235Notes

Reaction equation

HRID 2193235 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:17]([O:19][CH3:20])=[O:18])[C:6]2[CH:7]=[CH:8][C:9](=[O:16])[N:10]([CH2:13][CH:14]=O)[C:11]=2[CH:12]=1.[O:21]1[C:26]2[CH:27]=[CH:28][C:29]([CH2:31][N:32]([CH:40]3[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]3)[C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:30][C:25]=2[O:24][CH2:23][CH2:22]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(O)(=O)C.C(Cl)(Cl)Cl>[C:35]([O:34][C:33]([N:32]([CH2:31][C:29]1[CH:28]=[CH:27][C:26]2[O:21][CH2:22][CH2:23][O:24][C:25]=2[CH:30]=1)[CH:40]1[CH2:45][CH2:44][N:43]([CH2:14][CH2:13][N:10]2[C:11]3[CH:12]=[C:3]([O:2][CH3:1])[CH:4]=[C:5]([C:17]([O:19][CH3:20])=[O:18])[C:6]=3[CH:7]=[CH:8][C:9]2=[O:16])[CH2:42][CH2:41]1)=[O:39])([CH3:38])([CH3:36])[CH3:37]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 57815320Tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(piperidin-4-yl)carbamateHCID 59398121HCID 59398121, compound

Product 1

HCID 59398062HCID 59398062, compoundYield 75.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

To 10 mL of a chloroform solution containing 472 mg of methyl 7-methoxy-2-oxo-1-(2-oxoethyl)-1,2-dihydroquinoline-5-carboxylate and 374 mg of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(piperidin-4-yl)carbamate, 62 μL of acetic acid was added and stirred at room temperature for 1 hour. To the reaction mixture, 352 mg of sodium triacetoxyborohydride was added and stirred for 30 min. Aqueous saturated sodium hydrogen carbonate solution was added and the organic layer was separated. The organic layer was washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [Silica Gel; Kanto Chemical Co., Inc., Silica Gel 60, eluent; ethyl acetate:hexane=2:1], to give 493 mg of methyl 1-(2-(4-((tert-butoxycarbonyl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-5-carboxylate as a white solid.

Workup

  1. additionwas added
  2. stirringstirred for 30 min
  3. customthe organic layer was separated
  4. washThe organic layer was washed with aqueous saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by silica gel column chromatography [Silica Gel; Kanto Chemical Co., Inc., Silica Gel 60, eluent; ethyl acetate:hexane=2:1]

Sources & evidence

ORD record
ord-83d3969ebd114eb1b79048698d10104e
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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