Sodium Bicarbonate → tert-butyl (1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)(3-phenylpropyl)carbamate

HRID 2193164Notes

Reaction equation

HRID 2193164 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH3:17])=[CH:8][C:9](=[O:16])[N:10]2[CH2:13][CH:14]=O)=[CH:5][CH:4]=1.[C:18]([O:22][C:23](=[O:40])[N:24]([CH2:31][CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)([CH3:21])([CH3:20])[CH3:19].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(OCC)(=O)C.O.C(O)(=O)C.ClCCl>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH3:17])=[CH:8][C:9](=[O:16])[N:10]2[CH2:13][CH2:14][N:28]2[CH2:27][CH2:26][CH:25]([N:24]([CH2:31][CH2:32][CH2:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:23](=[O:40])[O:22][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:30][CH2:29]2)=[CH:5][CH:4]=1

Participants

9

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 59397837(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)acetaldehydeHCID 59398435Tert-butyl(3-phenylpropyl)(piperidin-4-yl)carbamate

Product 1

HCID 59398344tert-butyl (1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)(3-phenylpropyl)carbamateYield 117.9%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 3 mL of dichloromethane solution containing 95 mg of (7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)acetaldehyde, 81 mg of tert-butyl(3-phenylpropyl)(piperidin-4-yl)carbamate, 18 μl of acetic acid and 98 mg of sodium triacetoxyborohydride were added and stirred at room temperature for 1 hour. To the reaction mixture, water, ethyl acetate and aqueous saturated sodium hydrogen carbonate solution were added. The organic layer was separated, and washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to give 0.16 g of tert-butyl (1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)(3-phenylpropyl)carbamate as a brown foam.

Workup

  1. additionwere added
  2. customThe organic layer was separated
  3. washwashed with aqueous saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-72e3f7f1f67949cc97790788898a2893
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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