Hydrochloric Acid → HCID 21245053, compound

HRID 620727Notes

Reaction equation

HRID 620727 reaction equation
[CH2:1]([N:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]([N:11]([C:18](=O)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:5]1[CH2:26][O:27][CH3:28])[CH2:2][CH3:3].[BH4-].[Na+].B(F)(F)F.CCOCC.Cl>O1CCCC1>[CH2:1]([N:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]([N:11]([CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[C:5]1[CH2:26][O:27][CH3:28])[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8000Boron trifluoride etherateHCID 4311764Sodium borohydrideHCID 21245050HCID 21245050, compound

Product 1

HCID 21245053HCID 21245053, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

15 g of the compound prepared in Example 3, dissolved in 35 ml of tetrahydrofuran, were added under a nitrogen atmosphere to a reactor containing a suspension of 4.95 g of sodium borohydride in 100 ml of tetrahydrofuran, the temperature being maintained at 0° C. 29.6 ml of boron trifluoride etherate in 39 ml of tetrahydrofuran were then added dropwise. After the reaction medium had been allowed to return to room temperature, 69 ml of 10% strength hydrochloric acid were added. The solvent was then removed by distillation at atmospheric pressure, and the residue cooled and then alkalinized with caustic soda solution and then extracted with methylene chloride. After drying and evaporation of the solvent, the product was distilled, and then purified by preparative liquid chromatography on silica gel, using as solvent 2% strength and then 4% strength methanol in dichloromethane.

Workup

  1. additionwere added under a nitrogen atmosphere to a reactor
  2. additioncontaining
  3. customto return to room temperature
  4. customThe solvent was then removed by distillation at atmospheric pressure
  5. temperaturethe residue cooled
  6. extractionextracted with methylene chloride
  7. customAfter drying
  8. customevaporation of the solvent
  9. distillationthe product was distilled
  10. custompurified by preparative liquid chromatography on silica gel

Sources & evidence

ORD record
ord-4a39a09a9e48414c904897051c26b9d7
Source dataset
uspto-grants-1989_04
Patent number
US04822792

Reaction notes

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