Dichloromethane → HCID 59398332, compound

HRID 39834Notes

Reaction equation

HRID 39834 reaction equation
ClCCl.[CH:4]1([C:10]2[CH:19]=[C:18]3[C:13]([C:14]([CH3:24])=[CH:15][C:16](=[O:23])[N:17]3[CH2:20][CH:21]=O)=[CH:12][CH:11]=2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.[O:25]1[C:30]2[CH:31]=[CH:32][C:33]([CH2:35][N:36]([CH:44]3[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]3)[C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[CH:34][C:29]=2[O:28][CH2:27][CH2:26]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)(Cl)Cl.O.C(O)(=O)C>[CH:4]1([C:10]2[CH:19]=[C:18]3[C:13]([C:14]([CH3:24])=[CH:15][C:16](=[O:23])[N:17]3[CH2:20][CH2:21][N:47]3[CH2:48][CH2:49][CH:44]([N:36]([CH2:35][C:33]4[CH:32]=[CH:31][C:30]5[O:25][CH2:26][CH2:27][O:28][C:29]=5[CH:34]=4)[C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:40])[CH3:41])[CH2:45][CH2:46]3)=[CH:12][CH:11]=2)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 5049666Sodium triacetoxyborohydrideHCID 57815320Tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(piperidin-4-yl)carbamateHCID 59397891(7-Cyclohexyl-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)acetaldehyde

Product 1

HCID 59398332HCID 59398332, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To 1.5 mL of dichloromethane solution containing 56 mg of (7-cyclohexyl-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)acetaldehyde, 69 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 5 min. To the reaction mixture, 63 mg of sodium triacetoxyborohydride was added, and stirred for 45 min. Water and chloroform were added, the organic layer was separated, 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 73 mg of tert-butyl (1-(2-(7-cyclohexyl-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 45 min
  3. customthe organic layer was separated
  4. washwashed sequentially with water and 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 [eluent; hexane:ethyl acetate=1:2]

Sources & evidence

ORD record
ord-2d1e9205980a4071b5dfdba4e5a98a8a
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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