Dichloromethane → HCID 59398181, compound

HRID 2193132Notes

Reaction equation

HRID 2193132 reaction equation
ClCCl.[CH3:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([CH3:20])=[CH:11][C:12](=[O:19])[N:13]2[CH2:16][CH:17]=O)=[CH:8][CH:7]=1.[C:21]([O:25][C:26](=[O:45])[N:27]([CH2:34][C:35]1[CH:44]=[CH:43][C:38]2[O:39][CH2:40][CH2:41][O:42][C:37]=2[CH:36]=1)[CH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)([CH3:24])([CH3:23])[CH3:22].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(OCC)(=O)C.O.C(O)(=O)C>[C:21]([O:25][C:26](=[O:45])[N:27]([CH2:34][C:35]1[CH:44]=[CH:43][C:38]2[O:39][CH2:40][CH2:41][O:42][C:37]=2[CH:36]=1)[CH:28]1[CH2:33][CH2:32][N:31]([CH2:17][CH2:16][N:13]2[C:14]3[C:9](=[CH:8][CH:7]=[C:6]([O:5][CH3:4])[CH:15]=3)[C:10]([CH3:20])=[CH:11][C:12]2=[O:19])[CH2:30][CH2:29]1)([CH3:24])([CH3:22])[CH3:23]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 5049666Sodium triacetoxyborohydrideHCID 57815320Tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(piperidin-4-yl)carbamateHCID 59397837(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)acetaldehyde

Product 1

HCID 59398181HCID 59398181, compoundYield 62.8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 5 mL of a dichloromethane solution containing 64 mg of (7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)acetaldehyde, 0.11 g of tert-butyl(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(piperidin-4-yl)carbamate and 16 μl of acetic acid were added and stirred for 1 hour. To the reaction mixture, 89 mg of sodium triacetoxyborohydride was added and stirred for 1 hour. Water and ethyl acetate were added, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and extracts were combined, 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 [eluent; chloroform] to give 98 mg of tert-butyl(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate as a yellow oil.

Workup

  1. additionwere added
  2. stirringstirred for 1 hour
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washwashed with 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; chloroform]

Sources & evidence

ORD record
ord-0352219ac6aa40a1ae7d92ba2d94169e
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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