Acetic Acid → tert-butyl (1-(2-(7-methoxy-2-oxo-1,8-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

HRID 385511Notes

Reaction equation

HRID 385511 reaction equation
[CH3:1][O:2][C:3]1[N: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.[NH:17]1[CH2:22][CH2:21][CH:20]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:19][CH2:18]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.O>[CH3:1][O:2][C:3]1[N:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=[O:16])[N:10]2[CH2:13][CH2:14][N:17]2[CH2:18][CH2:19][CH:20]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[CH2:21][CH2:22]2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7238334-(N-Boc-amino)piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 57815463(7-methoxy-2-oxo-1,8-naphthyridin-1(2H)-yl)acetaldehyde

Product 1

HCID 57815232tert-butyl (1-(2-(7-methoxy-2-oxo-1,8-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamateYield 94.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.6 g of (7-methoxy-2-oxo-1,8-naphthyridin-1(2H)-yl)acetaldehyde in 70 mL of dichloromethane, 1.5 g of tert-butyl (piperidin-4-yl)carbamate and 0.42 mL of acetic acid were added, the mixture was stirred for 20 minutes, then 2.3 g of sodium triacetoxyborohydride was added to the reaction mixture and the mixture was stirred at room temperature for 2 hours 10 minutes. Thereto were added water, a saturated aqueous sodium hydrogen carbonate solution and chloroform, the organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, the resultant solution was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography using an eluent of chloroform:methanol=50:1 to obtain 2.8 g of tert-butyl (1-(2-(7-methoxy-2-oxo-1,8-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate as a white foam.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours 10 minutes
  2. customa saturated aqueous sodium hydrogen carbonate solution and chloroform, the organic layer was separated
  3. extractionthe aqueous layer was extracted with chloroform
  4. washthe resultant solution was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resultant residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a4d5b1c9f8a644b490c6993a13c06e19
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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