Tetrahydrofuran → HCID 59398315, compound

HRID 2193281

Reaction equation

HRID 2193281 reaction equation
O1CCCC1.[C:6]([O:10][C:11](=[O:51])[N:12]([CH2:40][C:41]1[CH:50]=[CH:49][C:44]2[O:45][CH2:46][CH2:47][O:48][C:43]=2[CH:42]=1)[CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][N:21]2[C:30]3[C:25](=[C:26]([C:33](=[O:38])N(OC)C)[CH:27]=[C:28]([O:31][CH3:32])[CH:29]=3)[CH:24]=[CH:23][C:22]2=[O:39])[CH2:15][CH2:14]1)([CH3:9])([CH3:8])[CH3:7].[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.[Cl-].[NH4+]>C(OCC)(=O)C>[C:6]([O:10][C:11](=[O:51])[N:12]([CH2:40][C:41]1[CH:50]=[CH:49][C:44]2[O:45][CH2:46][CH2:47][O:48][C:43]=2[CH:42]=1)[CH:13]1[CH2:14][CH2:15][N:16]([CH2:19][CH2:20][N:21]2[C:30]3[C:25](=[C:26]([CH:33]=[O:38])[CH:27]=[C:28]([O:31][CH3:32])[CH:29]=3)[CH:24]=[CH:23][C:22]2=[O:39])[CH2:17][CH2:18]1)([CH3:9])([CH3:7])[CH3:8]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 59398223tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(7-methoxy-5-((methoxy)(methyl)carbamoyl)-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamateHCID 86583787Diisobutylaluminumhydride toluene

Product 1

HCID 59398315HCID 59398315, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 20 mL of a tetrahydrofuran solution containing 1.05 g of tert-butyl(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(7-methoxy-5-((methoxy)(methyl)carbamoyl)-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate, 4.95 mL of 1 mol/L diisobutyl aluminum hydride/toluene was added at −78° C. and stirred for 1 hour. To the reaction mixture, aqueous saturated ammonium chloride solution and ethyl acetate were added. The organic layer was separated, washed sequentially with aqueous saturated sodium hydrogen carbonate solution 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 [Silica Gel; Kanto Chemical Co., Inc., Silica Gel 60N, eluent; chloroform:methanol=10:1], to give 0.65 g of tert-butyl(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(5-formyl-7-methoxy-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate as a colorless oil.

Workup

  1. additionwas added at −78° C.
  2. customThe organic layer was separated
  3. washwashed sequentially with aqueous saturated sodium hydrogen carbonate solution and aqueous saturated sodium chloride solution
  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 [Silica Gel; Kanto Chemical Co., Inc., Silica Gel 60N, eluent; chloroform:methanol=10:1]

Sources & evidence

ORD record
ord-8191a19d622943808eadf9b590446e0f
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Linked notes

Loading…