Hydrochloric Acid → HCID 178514939, compound

HRID 279149Notes

Reaction equation

HRID 279149 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]23[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]2[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]3=[O:19])[N:3]=[CH:2]1.[OH-].[Na+].[BH4-].[Na+].Cl>C(O)C.O>[NH:1]1[CH:5]=[C:4]([C:6]23[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]2[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]3[OH:19])[N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 4311764Sodium borohydrideHCID 178514938HCID 178514938, compound

Product 1

HCID 178514939HCID 178514939, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

9a-(1H-Imidazol-4-yl)-1,2,3,4,4a,9a-hexahydrofluoren-9-one (0.41 g) was dissolved in ethanol (10 ml). 48% NaOH solution (0.003 ml) and NaBH4 (0.06 g) was added and the mixture was heated at 40° C. for 12 hours. Water (2.5 ml) was added and the mixture was cooled to the ambient temperature. HCl (0.3 ml of 30% HCl in 1 ml H2O) was added and the mixture was stirred for 5 minutes. NaOH (0.2 ml of 48% NaOH in 5 ml H2O) was then added and the solvents were evaporated. The residue was mixed with water (30 ml) and extracted with CH2Cl2 (3×30 ml) and evaporated. The crude product was purified by flash chromatography using methylene chloride/methanol (95:5) as eluent. The yield was 0.26 g.

Workup

  1. temperaturethe mixture was cooled to the ambient temperature
  2. customthe solvents were evaporated
  3. additionThe residue was mixed with water (30 ml)
  4. extractionextracted with CH2Cl2 (3×30 ml)
  5. customevaporated
  6. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-85603dcee5f04719b80024859212eae0
Source dataset
uspto-grants-2002_03
Patent number
US06362211B1

Reaction notes

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