Sodium Bicarbonate → HCID 59398224, compound

HRID 39830Notes

Reaction equation

HRID 39830 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([N:7]=[CH:8][C:9](=[O:16])[N:10]2[CH2:13][CH:14]=O)=[CH:5][CH:4]=1.[O:17]1[C:22]2[CH:23]=[CH:24][C:25]([CH2:27][N:28]([CH:36]3[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]3)[C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:26][C:21]=2[O:20][CH2:19][CH2:18]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>O.C(Cl)(Cl)Cl.C(O)(=O)C.ClCCl>[O:17]1[C:22]2[CH:23]=[CH:24][C:25]([CH2:27][N:28]([CH:36]3[CH2:41][CH2:40][N:39]([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)[N:7]=[CH:8][C:9]4=[O:16])[CH2:38][CH2:37]3)[C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:32])[CH3:33])=[CH:26][C:21]=2[O:20][CH2:19][CH2:18]1

Participants

9

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 57815320Tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(piperidin-4-yl)carbamateHCID 59398142(7-methoxy-2-oxoquinoxalin-1(2H)-yl)acetaldehyde

Product 1

HCID 59398224HCID 59398224, compoundYield 47.7%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To 2.0 mL of dichloromethane solution containing 70 mg of (7-methoxy-2-oxoquinoxalin-1(2H)-yl)acetaldehyde, 0.11 g of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(piperidin-4-yl)carbamate and 20 μL of acetic acid were added, and stirred at room temperature for 20 min. To the reaction mixture, 0.10 g of sodium triacetoxyborohydride was added, and stirred at the same temperature for 2 hours. Chloroform and water were added, and aqueous saturated sodium hydrogen carbonate solution was added to make the pH 8.0 or more. 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; hexane:ethyl acetate=1:2], to give 83 mg of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate as a brown oil.

Workup

  1. additionwere added
  2. stirringstirred at the same temperature for 2 hours
  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; hexane:ethyl acetate=1:2]

Sources & evidence

ORD record
ord-feac9c331fb84c1a9c52962fbfaa3d75
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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