Butanal → HCID 24852913, compound

HRID 551801Notes

Reaction equation

HRID 551801 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[CH2:11][CH2:10][N:9]([C:12]([N:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[NH:17][CH2:16][CH2:15]3)=[O:13])[CH2:8]2)[CH:2]=1.[CH:24](=O)[CH2:25][CH2:26][CH3:27].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCl>[CH2:24]([N:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:14]([C:12]([N:9]2[CH2:10][CH2:11][CH:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[CH2:8]2)=[O:13])[CH2:15][CH2:16]1)[CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 261ButanalHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 67188496HCID 67188496, compound

Product 1

HCID 24852913HCID 24852913, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.2 g of 1-[(3-(pyridin-3-yl)pyrrolidin-1-yl)carbonyl]-1,2,3,4-tetrahydroquinoxaline, dissolved in 22 ml of dichloromethane, is introduced into a 100 ml round-bottomed flask. 0.29 ml of N-butyraldehyde is subsequently added, followed by 0.27 g of sodium triacetoxyborohydride, and the reaction mixture is stirred for eighteen hours. A saturated aqueous sodium hydrogencarbonate solution is added and then the aqueous phase is extracted three times with dichloromethane. The organic phases are combined and dried over sodium sulfate and the solvent is evaporated under reduced pressure. The residue is chromatographed on silica gel with a dichloromethane/methanol 95/5 mixture. 0.032 g of 1-butyl-4-[(3-(pyridin-3-yl)pyrrolidin-1-yl)carbonyl]-1,2,3,4-tetrahydroquinoxaline is obtained.

Workup

  1. additionis introduced into a 100 ml round-bottomed flask
  2. extractionthe aqueous phase is extracted three times with dichloromethane
  3. dry with materialdried over sodium sulfate
  4. customthe solvent is evaporated under reduced pressure
  5. customThe residue is chromatographed on silica gel with a dichloromethane/methanol 95/5 mixture

Sources & evidence

ORD record
ord-edc7d20595bd487aab2fef4cdad6c65e
Source dataset
uspto-grants-2011_05
Patent number
US07947834B2

Reaction notes

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