2,3-Dihydro-1,4-benzodioxin-6-carbaldehyde → HCID 59397828, compound

HRID 39798Notes

Reaction equation

HRID 39798 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[CH2:33][CH2:32][O:31][C:30]2[CH:34]=[C:35]([CH:38]=O)[CH:36]=[CH:37][C:29]1=2.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.O.C(O)(=O)C.ClCCl>[O:28]1[C:29]2[CH:37]=[CH:36][C:35]([CH2:38][N:19]3[CH2:20][CH2:21][C:16]([CH2:15][CH2:14][CH2:13][N:10]4[C:11]5[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=5)[CH:7]=[CH:8][C:9]4=[O:27])([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:17][CH2:18]3)=[CH:34][C:30]=2[O:31][CH2:32][CH2:33]1

Participants

9

Reactant 4

HCID 2481272,3-Dihydro-1,4-benzodioxin-6-carbaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 59398137ethyl 4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylate

Product 1

HCID 59397828HCID 59397828, compoundYield 89.4%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To 2 mL of dichloromethane solution containing 80 mg of ethyl 4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylate, 40 mg of 2,3-dihydrobenzo(b)(1,4)dioxin-6-carbaldehyde and 14 μL of acetic acid were added at room temperature, 78 mg of sodium triacetoxyborohydride was added under ice-cooling, and stirred at room temperature for 1 hour. To the reaction mixture, water, chloroform and aqueous saturated sodium hydrogen carbonate solution were added. The organic layer was separated, washed with aqueous saturated sodium chloride solution, 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=15:1], to give 0.10 g of ethyl 1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylate as a yellow oil.

Workup

  1. additionwere added at room temperature
  2. temperaturecooling
  3. customThe organic layer was separated
  4. washwashed with aqueous saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by silica gel column chromatography [eluent; chloroform:methanol=15:1]

Sources & evidence

ORD record
ord-4fc652af3fd949a8950929f493cfb1f5
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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