Sodium Bicarbonate → HCID 59398271, compound

HRID 2193267Notes

Reaction equation

HRID 2193267 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]([CH2:14][CH:15]=O)[C:4](=[O:17])[CH:3]=1.[O:18]1[C:23]2[CH:24]=[CH:25][C:26]([CH2:28][N:29]([CH:37]3[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]3)[C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:27][C:22]=2[O:21][CH2:20][CH2:19]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(O)(=O)C.C(Cl)(Cl)Cl>[O:18]1[C:23]2[CH:24]=[CH:25][C:26]([CH2:28][N:29]([CH:37]3[CH2:42][CH2:41][N:40]([CH2:15][CH2:14][N:5]4[C:6]5[C:11](=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=5)[C:2]([CH3:1])=[CH:3][C:4]4=[O:17])[CH2:39][CH2:38]3)[C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:33])[CH3:34])=[CH:27][C:22]=2[O:21][CH2:20][CH2:19]1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 57815320Tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(piperidin-4-yl)carbamateHCID 59398378HCID 59398378, compound

Product 1

HCID 59398271HCID 59398271, compoundYield 80.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

To 25 mL of a chloroform solution containing 71 mg of (4-methyl-6-methoxy-2-oxoquinolin-1(2H)-yl)acetaldehyde and 108 mg of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(piperidin-4-yl)carbamate, 18 μL of acetic acid was added, and stirred at room temperature for 1 hour. To the reaction mixture, 121 mg of sodium triacetoxyborohydride was added, and stirred for 2 hours. Aqueous saturated sodium hydrogen carbonate solution was added, the organic layer was separated. The organic layer was 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 [Silica Gel; Kanto Chemical Co., Inc., Silica Gel 60, eluent; chloroform:methanol=20:1], to give 140 mg of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(4-methyl-6-methoxy-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate as a white solid.

Workup

  1. additionwas added
  2. stirringstirred for 2 hours
  3. customthe organic layer was separated
  4. washThe organic layer was washed 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 [Silica Gel; Kanto Chemical Co., Inc., Silica Gel 60, eluent; chloroform:methanol=20:1]

Sources & evidence

ORD record
ord-b4e2d370318f41e19f83e0451b96b30c
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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