Sodium Bicarbonate → HCID 59398018, compound

HRID 2193197Notes

Reaction equation

HRID 2193197 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:16])=[CH:7][C:8](=[O:15])[N:9]2[CH2:12][CH:13]=O)=[CH:4][CH:3]=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+]>C(Cl)(Cl)Cl.O.C(O)(=O)C.ClCCl>[C:31]([O:30][C:29](=[O:35])[N:28]([CH2:27][C:25]1[CH:24]=[CH:23][C:22]2[O:17][CH2:18][CH2:19][O:20][C:21]=2[CH:26]=1)[CH:36]1[CH2:41][CH2:40][N:39]([CH2:13][CH2:12][N:9]2[C:10]3[C:5](=[CH:4][CH:3]=[C:2]([F:1])[CH:11]=3)[C:6]([CH3:16])=[CH:7][C:8]2=[O:15])[CH2:38][CH2:37]1)([CH3:34])([CH3:32])[CH3:33]

Participants

9

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 57815320Tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(piperidin-4-yl)carbamateHCID 59398124HCID 59398124, compound

Product 1

HCID 59398018HCID 59398018, compoundYield 92.3%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To 2.5 mL of dichloromethane solution containing 83 mg of (7-fluoro-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)acetaldehyde, 0.13 g of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(piperidin-4-yl)carbamate and 25 μL of acetic acid were added, and stirred for 1 hour. To the reaction mixture, 0.12 g of sodium triacetoxyborohydride was added, and stirred for 50 min. Water and chloroform were added, and adjusted to pH 10.0 with aqueous saturated sodium hydrogen carbonate solution. 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=1:3], to give 0.19 g of tert-butyl(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(7-fluoro-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)ethyl)piperidin-4-yl)carbamate as a colorless oil.

Workup

  1. additionwere added
  2. stirringstirred for 50 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; hexane:ethyl acetate=1:3]

Sources & evidence

ORD record
ord-29a9f3be9f5c44f8ae5320b62f4f5e8a
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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