Acetic Acid → 1,2,3,4-Tetrahydro-7-phenylmethoxycyclopent[b]indole-2-carboxylic acid ethyl ester

HRID 2226921Notes

Reaction equation

HRID 2226921 reaction equation
C(O)(=O)C.Cl.[C:6]1([CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20]N)=[CH:16][CH:15]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:22]([O:24][C:25]([CH:27]1[CH2:31][CH2:30][C:29](=O)[CH2:28]1)=[O:26])[CH3:23]>O>[CH2:22]([O:24][C:25]([CH:27]1[CH2:31][C:30]2[NH:20][C:17]3[CH:16]=[CH:15][C:14]([O:13][CH2:12][C:6]4[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=4)=[CH:19][C:18]=3[C:29]=2[CH2:28]1)=[O:26])[CH3:23]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 223136Ethyl 3-oxocyclopentanecarboxylateHCID 3016725(4-(Benzyloxy)phenyl)hydrazine monohydrochloride

Product 1

HCID 541882621,2,3,4-Tetrahydro-7-phenylmethoxycyclopent[b]indole-2-carboxylic acid ethyl esterYield 59.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 250 ml of 80% acetic acid in water, were added 4-phenylmethoxyphenylhydrazine hydrochloride (30 g, 0.12 mole) and 3-oxocyclopentane carboxylic acid ethyl ester (20 g, 0.13 mole). After stirring at ambient temperature for one hour and then at 100° C. for four hours, the mixture was cooled and poured into one liter of water. After stirring for five minutes, the mixture was extracted with ethyl acetate (3×). The organic layer was washed successively with water (2×) and saturated sodium chloride solution, and thereafter dried over anhydrous MgSO4. After filtering, the solution was concentrated to a dark oil (~48 g), which was eluted on a silica gel column with 5% ethyl acetate/dichloromethane via HPLC. The desired fractions were combined and concentrated to give the product as a thick brown oil (24.1 g).

Workup

  1. waitat 100° C. for four hours
  2. temperaturethe mixture was cooled
  3. stirringAfter stirring for five minutes
  4. extractionthe mixture was extracted with ethyl acetate (3×)
  5. washThe organic layer was washed successively with water (2×) and saturated sodium chloride solution
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationAfter filtering
  8. concentrationthe solution was concentrated to a dark oil (~48 g), which
  9. washwas eluted on a silica gel column with 5% ethyl acetate/dichloromethane via HPLC
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-faadc4a600154045b252b522f906083a
Source dataset
uspto-grants-1994_09
Patent number
US05350762

Reaction notes

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