Hydrochloric Acid → HCID 66625010, compound

HRID 1629671Notes

Reaction equation

HRID 1629671 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[N:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][O:22][Si:23]([C:36]([CH3:39])([CH3:38])[CH3:37])([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:17][CH:16]=2)[CH2:6][CH:5]1[CH3:40])(=[O:3])[CH3:2].[BH4-].[Na+].O.O.O.O.O.O.O.[Cl-].[Cl-].[Cl-].[Ce+3].Cl.C(=O)([O-])O.[Na+]>CO>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][O:22][Si:23]([C:36]([CH3:39])([CH3:38])[CH3:37])([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[CH:17][CH:16]=2)[CH2:6][CH:5]1[CH3:40])(=[O:3])[CH3:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 21585214Cerium trichloride heptahydrateHCID 66624871HCID 66624871, compound

Product 1

HCID 66625010HCID 66625010, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

[Step 2] 715 mg of 1-acetyl-2-methyl-4-[(4-tert-butyldiphenylsilyloxymethylphenyl)imino]-1,2,3,4-tetrahydroquinoline, 74 mg of sodium borohydride, and 488 mg of cerium trichloride heptahydrate were dissolved in 8 mL of methanol, and the solution was stirred for 2 hours at 50° C. After completion of the reaction, 1 N hydrochloric acid was added to the reaction liquid, and the mixture was stirred for 30 minutes. The reaction liquid was neutralized with a saturated aqueous solution of sodium hydrogen carbonate, and then was extracted with chloroform. The organic layer was washed with a saturated solution of sodium hydrogen carbonate and saturated brine, dehydrated with anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by using silica gel chromatography (hexane:ethyl acetate 1:1), and thus 615 mg (85%) of 1-acetyl-4-[(4-tert-butyldiphenylsilyloxymethylphenyl)amino]-2-methyl-1,2,3,4-tetrahydroquinoline was obtained as a yellow oily substance (cis:trans=3:1).

Workup

  1. additionwas added to the reaction liquid
  2. stirringthe mixture was stirred for 30 minutes
  3. customThe reaction liquid
  4. extractionwas extracted with chloroform
  5. washThe organic layer was washed with a saturated solution of sodium hydrogen carbonate and saturated brine
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified

Sources & evidence

ORD record
ord-8fd609d71e3245ddaa94af9ebb92cbb0
Source dataset
uspto-grants-2014_07
Patent number
US08791090B2

Reaction notes

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