Hydrochloric Acid → HCID 178419203, compound

HRID 875292Notes

Reaction equation

HRID 875292 reaction equation
[Cl-].[Ce+3].[Cl-].[Cl-].[BH4-:5].[Na+].[CH3:7][N:8]([CH3:26])[C:9]1[CH:14]=[CH:13][C:12]([PH:15](=O)[C:16]2[CH:21]=[CH:20][C:19]([N:22]([CH3:24])[CH3:23])=[CH:18][CH:17]=2)=[CH:11][CH:10]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl.[OH-].[Na+]>O1CCCC1.C1(C)C=CC=CC=1.O>[CH3:7][N:8]([CH3:26])[C:9]1[CH:10]=[CH:11][C:12]([PH:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]([CH3:24])[CH3:23])=[CH:18][CH:17]=2)=[CH:13][CH:14]=1.[BH3:5]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24636Cerium(III) chlorideHCID 4311764Sodium borohydrideHCID 21226445Aluminium lithium hydrideHCID 178482907HCID 178482907, compound

Product 1

HCID 178419203HCID 178419203, compoundYield 20.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere, a solution of cerium chloride (7.69 g, 3.0 equivalents) in tetrahydrofuran (25 mL) was stirred at room temperature (25° C.) for 30 min. After addition of sodium borohydride (1.22 g, 3.1 equivalents), the mixture was stirred at room temperature for 1 hr. After bis(4-dimethylaminophenyl)-phosphine oxide (3.0 g, 10.4 mmoL) synthesized in Reference Example 6 and lithium aluminum hydride (0.47 g, 1.2 equivalents) were successively added to the mixture at 5° C., the mixture was stirred at room temperature for 3 hr. Water (20 mL) was added to the mixture at 3° C., and then toluene (40 mL) and 6M hydrochloric acid (10 mL) were added thereto, and the mixture was stirred at room temperature for 30 min. The reaction mixture was neutralized with sodium hydroxide, and the mixture was partitioned. The aqueous layer was extracted with tetrahydrofuran (50 mL). The combined organic layer was successively washed with 5% brine (20 mL). The organic layer was dried over anhydrous magnesium sulfate and filtered naturally, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel 5 g, n-hexane/ethyl acetate=1/1). The residue was recrystallized from n-heptane to give the title compound (0.61 g, white crystals). yield 20.5%. melting point 142.6° C.

Workup

  1. additionwere successively added to the mixture at 5° C.
  2. stirringthe mixture was stirred at room temperature for 3 hr
  3. stirringthe mixture was stirred at room temperature for 30 min
  4. customthe mixture was partitioned
  5. extractionThe aqueous layer was extracted with tetrahydrofuran (50 mL)
  6. washThe combined organic layer was successively washed with 5% brine (20 mL)
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. filtrationfiltered naturally
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe residue was purified by column chromatography (silica gel 5 g, n-hexane/ethyl acetate=1/1)
  11. customThe residue was recrystallized from n-heptane

Sources & evidence

ORD record
ord-c55981248a624ac480d297330432e78b
Source dataset
uspto-grants-2015_03
Patent number
US08981147B2

Reaction notes

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