Benzyl chloroformate → HCID 69645639, compound

HRID 1713483Notes

Reaction equation

HRID 1713483 reaction equation
C1(C[N:8]2[CH2:13][CH2:12][N:11](CC3C=CC=CC=3)[CH2:10][CH:9]2[C:21]([CH:26]2[CH2:28][CH2:27]2)([CH:23]2[CH2:25][CH2:24]2)[OH:22])C=CC=CC=1.[C:29](=[O:32])([O-:31])O.[Na+].[C:34](Cl)(=[O:43])[O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(O)C.O.[C].[Pd]>[C:37]1([CH2:36][O:31][C:29]([N:8]2[CH2:13][CH2:12][N:11]([C:34]([O:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[O:43])[CH2:10][CH:9]2[C:21]([CH:26]2[CH2:28][CH2:27]2)([CH:23]2[CH2:25][CH2:24]2)[OH:22])=[O:32])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 23121930HCID 23121930, compound

Product 1

HCID 69645639HCID 69645639, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 19096565Water ethanolSolvent

Procedure

1,4-Bis(phenylmethyl)-α,α-dicyclopropyl-2-piperazinemethanol (1.2 g, 3.1 mmol) was dissolved in ethanol/water (40 mL/4 mL). 10% Palladium carbon (0.12 g) was added thereto, and the mixture was stirred under hydrogen pressure (3.6 bar) at room temperature one whole day and night. The reaction solution was filtered through a Celite, the Celite was washed with ethanol, and then the filtrate was concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (50 ml). A 0.5 M aqueous sodium hydrogen carbonate solution (50 mL) and benzyl chlorocarbonate (1.8 mL, 12 mmol) were added thereto. The resulting mixture was stirred at room temperature for 4 hours and the reaction solution was extracted with ethyl acetate (100 mL). The extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. Then, the residue was purified with silica gel column chromatography (hexane:ethyl acetate=21:1 to 4:1) to obtain the title compound (1.4 g, quantitative) as an oily matter.

Workup

  1. filtrationThe reaction solution was filtered through a Celite
  2. washthe Celite was washed with ethanol
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in tetrahydrofuran (50 ml)
  5. stirringThe resulting mixture was stirred at room temperature for 4 hours
  6. extractionthe reaction solution was extracted with ethyl acetate (100 mL)
  7. washThe extract was washed with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThen, the residue was purified with silica gel column chromatography (hexane:ethyl acetate=21:1 to 4:1)

Sources & evidence

ORD record
ord-baade2f103184edd8c01a05ef6d135d4
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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