Hydrochloric Acid → 2-(5-Methoxyhept-1-yl)bicyclo[3.3.0]octane

HRID 1722387Notes

Reaction equation

HRID 1722387 reaction equation
[CH3:1][O:2][CH:3]([CH2:17][CH3:18])[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:15][CH2:14][CH:13]2[CH:9]1[CH2:10][C:11](=O)[CH2:12]2.[OH-].[K+].O.NN.Cl>C(O)COCCO>[CH3:1][O:2][CH:3]([CH2:17][CH3:18])[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:15][CH2:14][CH:13]2[CH:9]1[CH2:10][CH2:11][CH2:12]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 55994Cioteronel

Product 1

HCID 150530492-(5-Methoxyhept-1-yl)bicyclo[3.3.0]octane

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Conditions

Temperature
95 °C

Procedure

2-(5-Methoxyhept-1-y)bicyclo[3.3.0]octan-7-one {hexahydro-4-(5-methoxyheptyl)-2(1H)-pentalenone} (5 g, 19.8 mmoles) is mixed with diethylene glycol (27 ml) and potassium hydroxide (3.8 g, 6.7 mmoles). The reaction is stirred and mixed with 80% hydrazine hydrate (2.8 ml, 7.0 mmoles). The reaction is heated to 95° C. for 2 hours. After which time the temperature is increased to 200° C. and maintained with stirring for 5 hours. Then the reaction is cooled and added to 6N hydrochloric acid (200 ml). The solution is partitioned between ether and the phases separated. The aqueous phase is extracted with ether (2×100 ml) and the extracts combined. The ether solution is dried over anhydrous magnesium sulfate and the solvent removed under vacuum leaving a clear, purple oil. The crude product is kugelrohred under reduced pressure leaving a clear, colorless oil (4.0 g, 16.8 mmoles).

Workup

  1. temperatureAfter which time the temperature is increased to 200° C.
  2. temperaturemaintained
  3. stirringwith stirring for 5 hours
  4. temperatureThen the reaction is cooled
  5. customThe solution is partitioned between ether
  6. customthe phases separated
  7. extractionThe aqueous phase is extracted with ether (2×100 ml)
  8. dry with materialThe ether solution is dried over anhydrous magnesium sulfate
  9. customthe solvent removed under vacuum
  10. customleaving a clear, purple oil

Sources & evidence

ORD record
ord-862f423c05e84f4d9669a68fed4a10c1
Source dataset
uspto-grants-1989_08
Patent number
US04855322

Reaction notes

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