Sodium Bicarbonate → HCID 59398059, compound

HRID 2193214Notes

Reaction equation

HRID 2193214 reaction equation
[CH:1]1([O:4][C:5]2[CH:14]=[C:13]3[C:8]([C:9]([CH3:19])=[CH:10][C:11](=[O:18])[N:12]3[CH2:15][CH:16]=O)=[CH:7][CH:6]=2)[CH2:3][CH2:2]1.[O:20]1[C:25]2[CH:26]=[CH:27][C:28]([CH2:30][N:31]([CH:39]3[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]3)[C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:29][C:24]=2[O:23][CH2:22][CH2:21]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(O)(=O)C.ClCCl>[CH:1]1([O:4][C:5]2[CH:14]=[C:13]3[C:8]([C:9]([CH3:19])=[CH:10][C:11](=[O:18])[N:12]3[CH2:15][CH2:16][N:42]3[CH2:43][CH2:44][CH:39]([N:31]([CH2:30][C:28]4[CH:27]=[CH:26][C:25]5[O:20][CH2:21][CH2:22][O:23][C:24]=5[CH:29]=4)[C:32](=[O:38])[O:33][C:34]([CH3:36])([CH3:35])[CH3:37])[CH2:40][CH2:41]3)=[CH:7][CH:6]=2)[CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 57815320Tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(piperidin-4-yl)carbamateHCID 59398023HCID 59398023, compound

Product 1

HCID 59398059HCID 59398059, compoundYield 72.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To 2 mL of dichloromethane solution containing 60 mg of (7-cyclopropoxy-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)acetaldehyde, 81 mg of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(piperidin-4-yl)carbamate and 20 μL of acetic acid were added, and stirred for 15 min. To the reaction mixture, 74 mg of sodium triacetoxyborohydride was added, and stirred for 40 min. Chloroform and aqueous saturated sodium hydrogen carbonate solution were added, the organic layer was separated, washed sequentially with water and 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 [eluent; hexane:ethyl acetate=1:4], to give 0.10 g of tert-butyl (1-(2-(7-cyclopropoxy-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)ethyl)piperidin-4-yl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)carbamate as a colorless oil.

Workup

  1. additionwere added
  2. stirringstirred for 40 min
  3. customthe organic layer was separated
  4. washwashed sequentially with water and 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 [eluent; hexane:ethyl acetate=1:4]

Sources & evidence

ORD record
ord-483348acc6154ff09dd4f24655630409
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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