Water → HCID 59323459, compound

HRID 2390060Notes

Reaction equation

HRID 2390060 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:37]=[CH:38][CH:39]=1)[CH2:7][N:8]([CH2:16][CH2:17][N:18]1[CH:27]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23](F)[CH:24]=2)[CH2:19]1)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])([O-])=O.[BH4-].[Na+].O>CO.[Ni](Cl)Cl>[NH2:1][C:4]1[CH:5]=[C:6]([CH:37]=[CH:38][CH:39]=1)[CH2:7][N:8]([CH2:16][CH2:17][N:18]1[CH:27]([CH2:28][C:29]2[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=2)[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19]1)[C:9](=[O:15])[O:10][C:11]([CH3:13])([CH3:14])[CH3:12]

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 59323399HCID 59323399, compound

Product 1

HCID 59323459HCID 59323459, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 887MethanolSolvent

Procedure

Under an argon atmosphere, 190 mg of tert-butyl 3-nitrobenzyl[2-[6-fluoro-3-(4-fluorobenzyl)-3,4-dihydroisoquinolin-2(1H)-yl]ethyl]carbamate was dissolved in 8 mL of methanol, followed by stirring under ice-cooling. 343 mg of nickel chloride.hexahydrate was added thereto, and then 73 mg of sodium borohydride was slowly added thereto. After completion of addition of a reagent, the reaction liquid was warmed to room temperature, followed by stirring for 10 minutes. After completion of the reaction, water was added to the reaction liquid, followed by extraction with chloroform. The organic layer was then washed with an aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 155 mg (yield 87%) of a title compound as a yellow oily substance.

Workup

  1. temperaturecooling
  2. additionAfter completion of addition of a reagent
  3. customthe reaction liquid
  4. stirringby stirring for 10 minutes
  5. additionwas added to the reaction liquid
  6. extractionfollowed by extraction with chloroform
  7. washThe organic layer was then washed with an aqueous sodium bicarbonate solution and saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cc0a43af373d48f1a199bde9aec80136
Source dataset
uspto-grants-2012_09
Patent number
US08273766B2

Reaction notes

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