Sodium Bicarbonate → tert-butyl {1-[2-(7-methoxy-2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate

HRID 2193063Notes

Reaction equation

HRID 2193063 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=[O:16])[N:10]2[CH2:13][CH:14]=O)=[CH:5][CH:4]=1.[C:17]([O:21][C:22](=[O:30])[NH:23][CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)([CH3:20])([CH3:19])[CH3:18].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>[C:17]([O:21][C:22](=[O:30])[NH:23][CH:24]1[CH2:29][CH2:28][N:27]([CH2:14][CH2:13][N:10]2[C:11]3[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=3)[CH:7]=[CH:8][C:9]2=[O:16])[CH2:26][CH2:25]1)([CH3:20])([CH3:18])[CH3:19]

Participants

9

Reactant 4

HCID 516892Sodium BicarbonateHCID 7238334-(N-Boc-amino)piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 59397833(7-methoxy-2-oxoquinolin-1(2H)-yl)acetaldehyde

Product 1

HCID 59371209tert-butyl {1-[2-(7-methoxy-2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 10 mL of a dichloromethane solution containing 0.23 g of (7-methoxy-2-oxoquinolin-1(2H)-yl)acetaldehyde, 0.21 g of tert-butyl(piperidin-4-yl)carbamate and 60 μL of acetic acid were added, and the mixture was stirred for 10 minutes. Thereto was added 0.34 g of sodium triacetoxyborohydride, and the mixture was stirred at room temperature for 4 hours and 30 minutes. The reaction mixture was added with water and ethyl acetate, and the reaction solution was neutralized with an aqueous saturated sodium hydrogen carbonate solution. The organic layer was separated, washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 0.43 g of a colorless oily substance, tert-butyl(1-(2-(7-methoxy-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate.

Workup

  1. additionwere added
  2. stirringthe mixture was stirred at room temperature for 4 hours and 30 minutes
  3. customThe organic layer was separated
  4. washwashed with an aqueous saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0f53b91e93e5406590d906100bc6fc8b
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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