Hydrochloric Acid → HCID 54070919, compound

HRID 1004615Notes

Reaction equation

HRID 1004615 reaction equation
C([N:3]1[C@H:11]2[C@@:6]([CH3:20])([C:7]([CH3:19])([CH3:18])[C:8]3[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[C:9]=3[CH2:10]2)[CH2:5][CH2:4]1)=O.Cl>C(O)CC.O>[CH3:17][O:16][C:12]1[C:9]2[CH2:10][C@@H:11]3[C@:6]([CH3:20])([CH2:5][CH2:4][NH:3]3)[C:7]([CH3:19])([CH3:18])[C:8]=2[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86755330HCID 86755330, compound

Product 1

HCID 54070919HCID 54070919, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 10311-PropanolSolvent

Procedure

9.6 g (35 mmol) of trans-1-formyl-8-methoxy-3a,4,4-trimethyl-2,3,3a,4,9,9a-hexahydro-1H-benz[f]indole (5) are dissolved in 75 mL of n-propanol and mixed with 25 mL of conc. hydrochloric acid and 15 mL of water. The mixture is refluxed for 12 h, the alcohol is eliminated in vacuo and diluted with 800 mL of water. The mixture is extracted once with 150 mL of ethyl acetate (discarded), the aqueous phase is made alkaline with sodium hydroxide and extracted three times with 200 mL ethyl acetate. The combined organic phases are dried over MgSO4 and the solvent is eliminated in vacuo. 8.6 g (100%) of trans-8-methoxy-3a,4,4-trimethyl-2,3,3a,4,9,9a-hexahydro-1H-benz[f]indole (6) are obtained as an oil.

Workup

  1. temperatureThe mixture is refluxed for 12 h
  2. extractionThe mixture is extracted once with 150 mL of ethyl acetate (discarded)
  3. extractionextracted three times with 200 mL ethyl acetate
  4. dry with materialThe combined organic phases are dried over MgSO4

Sources & evidence

ORD record
ord-9aa5e32bf0304c68a35571e5bf2cea1c
Source dataset
uspto-grants-2000_04
Patent number
US06051583

Reaction notes

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