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

HRID 2226923Notes

Reaction equation

HRID 2226923 reaction equation
C(O)(=O)C.C([O:7][C:8]([CH:10]1[CH2:29][C:13]2[NH:14][C:15]3[CH:16]=[CH:17][C:18]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:19][C:20]=3[C:12]=2[CH2:11]1)=[O:9])C>O>[C:23]1([CH2:22][O:21][C:18]2[CH:17]=[CH:16][C:15]3[NH:14][C:13]4[CH2:29][CH:10]([C:8]([OH:9])=[O:7])[CH2:11][C:12]=4[C:20]=3[CH:19]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 541882621,2,3,4-Tetrahydro-7-phenylmethoxycyclopent[b]indole-2-carboxylic acid ethyl ester

Product 1

HCID 189640221,2,3,4-Tetrahydro-7-phenylmethoxycyclopent[b]indole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

To 100 ml of 80% acetic acid in water, was added 1,2,3,4-tetrahydro-7-phenylmethoxycyclopent[b]indole-2-carboxylic acid ethyl ester (10 g, 0.03 mole). After stirring at 100° C. for four hours, the mixture was cooled, poured into 500 ml of water, stirred for five minutes, and extracted with ethyl acetate (3×). The organic layer was washed successively with water and saturated sodium chloride solution, and thereafter dried over anhydrous MgSO4. After filtering, the solution was concentrated to a dark oil (~10 g), which was eluted on a silica gel column with 5% ethyl acetate/dichloromethane via HPLC. The desired fractions were combined and concentrated to a tan solid, 1.3 g, m.p. 160°-162° C. This material was recrystallized from ether to give the product as a tan solid, 1.0 g, m.p. 161°-163° C.

Workup

  1. temperaturethe mixture was cooled
  2. stirringstirred for five minutes
  3. extractionextracted with ethyl acetate (3×)
  4. washThe organic layer was washed successively with water and saturated sodium chloride solution
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationAfter filtering
  7. concentrationthe solution was concentrated to a dark oil (~10 g), which
  8. washwas eluted on a silica gel column with 5% ethyl acetate/dichloromethane via HPLC
  9. concentrationconcentrated to a tan solid, 1.3 g, m.p. 160°-162° C
  10. customThis material was recrystallized from ether

Sources & evidence

ORD record
ord-c95cd5041e444df8bc89ca62b2dacf34
Source dataset
uspto-grants-1994_09
Patent number
US05350762

Reaction notes

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