Sodium Bicarbonate → HCID 59398320, compound

HRID 39858Notes

Reaction equation

HRID 39858 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=[O:27])[N:10]2[CH2:13][CH2:14][CH2:15][C:16]2([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[CH:5][CH:4]=1.[O:28]1[CH:32]=[CH:31][CH:30]=[C:29]1/[CH:33]=[CH:34]/[CH:35]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(O)(=O)C.ClCCl>[O:28]1[CH:32]=[CH:31][CH:30]=[C:29]1/[CH:33]=[CH:34]/[CH2:35][N:19]1[CH2:20][CH2:21][C:16]([CH2:15][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:27])([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:17][CH2:18]1

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 15495212-FuranacroleinHCID 5049666Sodium triacetoxyborohydrideHCID 59398137ethyl 4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylate

Product 1

HCID 59398320HCID 59398320, compoundYield 93.4%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To 2 mL of a dichloromethane solution containing 50 mg of ethyl 4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylate, 18 mg of (2E)-3-(2-furyl)acrolein and 20 μL of acetic acid were added, and stirred for 40 min. To the reaction mixture, 43 mg of sodium triacetoxyborohydride was added, stirred for 30 min. Chloroform and aqueous saturated sodium hydrogen carbonate solution were added, the organic layer was separated, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; chloroform:methanol=50:1], to give 60 mg of ethyl 1-((2E)-3-(2-furyl)-2-propen-1-yl)-4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylate as a brown solid.

Workup

  1. additionwere added
  2. stirringstirred for 30 min
  3. customthe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by silica gel column chromatography [eluent; chloroform:methanol=50:1]

Sources & evidence

ORD record
ord-1223ea47a52b4a738feee055f7167095
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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