Sodium Hydroxide → tert-butyl (1-(2-(2-oxo-1,7-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

HRID 385495Notes

Reaction equation

HRID 385495 reaction equation
[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][N:6]=[CH:7][CH:8]=2)[N:3]1[CH2:12][CH:13]=O.[NH:15]1[CH2:20][CH2:19][CH:18]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:17][CH2:16]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+].[OH-].[Na+]>ClCCl.C(Cl)(Cl)Cl.C(O)(=O)C>[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][N:6]=[CH:7][CH:8]=2)[N:3]1[CH2:12][CH2:13][N:15]1[CH2:16][CH2:17][CH:18]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:25])[CH3:27])[CH2:19][CH2:20]1

Participants

9

Reactant 5

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 7238334-(N-Boc-amino)piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 578151862-(2-oxo-1,7-naphthyridin-1(2H)-yl)acetaldehyde

Product 1

HCID 57815235tert-butyl (1-(2-(2-oxo-1,7-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamateYield 57.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.5 g of (2-oxo-1,7-naphthyridin-1(2H)-yl)acetaldehyde in 25 mL of dichloromethane, 2.6 g of tert-butyl (piperidin-4-yl)carbamate and 0.76 mL of acetic acid, and 4.2 g of sodium triacetoxyborohydride were added, and the mixture was stirred at room temperature for 4 hours and then left overnight. Thereto was added chloroform and the reaction mixture was adjusted to pH 9.1 with a saturated aqueous sodium hydrogen carbonate solution and a 20% aqueous sodium hydroxide solution. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, and the resultant solution was washed sequentially with water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. To the resultant residue, diethyl ether was added, and the solid was filtered off to obtain 2.8 g of tert-butyl (1-(2-(2-oxo-1,7-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate as a slightly yellow solid.

Workup

  1. waitleft overnight
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with chloroform
  4. washthe resultant solution was washed sequentially with water
  5. dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. additionTo the resultant residue, diethyl ether was added
  8. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-6a3857317a84410d8924566e5b17dc80
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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