Sodium Bicarbonate → HCID 59397906, compound

HRID 2193209Notes

Reaction equation

HRID 2193209 reaction equation
[CH:1]1([C:4]2[CH:13]=[C:12]3[C:7]([C:8]([CH3:18])=[CH:9][C:10](=[O:17])[N:11]3[CH2:14][CH:15]=O)=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.[O:19]1[C:24]2[CH:25]=[CH:26][C:27]([CH2:29][N:30]([CH:38]3[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]3)[C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:28][C:23]=2[O:22][CH2:21][CH2:20]1.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>[CH:1]1([C:4]2[CH:13]=[C:12]3[C:7]([C:8]([CH3:18])=[CH:9][C:10](=[O:17])[N:11]3[CH2:14][CH2:15][N:41]3[CH2:42][CH2:43][CH:38]([N:30]([CH2:29][C:27]4[CH:26]=[CH:25][C:24]5[O:19][CH2:20][CH2:21][O:22][C:23]=5[CH:28]=4)[C:31](=[O:37])[O:32][C:33]([CH3:35])([CH3:34])[CH3:36])[CH2:39][CH2:40]3)=[CH:6][CH:5]=2)[CH2:3][CH2:2]1

Participants

9

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 57815320Tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(piperidin-4-yl)carbamateHCID 59398306(7-Cyclopropyl-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)acetaldehyde

Product 1

HCID 59397906HCID 59397906, compoundYield 78.6%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To 1.5 mL of dichloromethane solution containing 53 mg of (7-cyclopropyl-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)acetaldehyde, 77 mg of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(piperidin-4-yl)carbamate and 15 μL of acetic acid were added, and stirred for 10 min. To the reaction mixture, 70 mg of sodium triacetoxyborohydride was added, and stirred for 30 min. Water, chloroform and aqueous saturated sodium hydrogen carbonate solution were added, the organic layer was separated, and the aqueous layer was neutralized with aqueous saturated sodium hydrogen carbonate solution, thereafter extracted with ethyl acetate. The organic layer and extracts were combined, washed sequentially with water and 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; hexane:ethyl acetate=1:2], to give 99 mg of tert-butyl (1-(2-(7-cyclopropyl-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)ethyl)piperidin-4-yl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)carbamate as a colorless oil.

Workup

  1. additionwere added
  2. stirringstirred for 30 min
  3. customthe organic layer was separated
  4. extractionextracted with ethyl acetate
  5. washwashed sequentially with water and aqueous saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by silica gel column chromatography [eluent; hexane:ethyl acetate=1:2]

Sources & evidence

ORD record
ord-d5d807fff10b4b9f8e050600c84d4617
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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