Water → HCID 178515457, compound

HRID 279138Notes

Reaction equation

HRID 279138 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]23[CH2:17][CH2:16][C:15](=[O:18])[CH:7]2[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=2[CH2:14]3)[N:3]=[CH:2]1.[BH4-].[Na+].O>C(O)C>[NH:1]1[CH:5]=[C:4]([C:6]23[CH2:17][CH2:16][CH:15]([OH:18])[CH:7]2[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=2[CH2:14]3)[N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 178515456HCID 178515456, compound

Product 1

HCID 178515457HCID 178515457, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
37.5 °C

Procedure

To a solution of 8a-(1H-imidazol-4-yl)-1,3a,8,8a-tetrahydro-2H-cyclopenta[a]inden-3-one (1 g) in 40 ml of ethanol was added 0.16 g of sodium borohydride under a nitrogen atmosphere. The reaction mixture was stirred at 35-40° C. for 4 hours and then poured into water (100 ml) and extracted with methylene chloride (3×100 ml). The combined organic layers were dried over sodium sulfate and the solvent removed under reduced pressure. The crude product was purified by flash chromatography using methylene chloride/methanol (95:5) as eluent. The yield was 0.6 g, m.p. 183-186° C.

Workup

  1. extractionextracted with methylene chloride (3×100 ml)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. customthe solvent removed under reduced pressure
  4. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-bb75a61c16f94c49ac554c959904b802
Source dataset
uspto-grants-2002_03
Patent number
US06362211B1

Reaction notes

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