Water → HCID 21272031, compound

HRID 1193477Notes

Reaction equation

HRID 1193477 reaction equation
[CH2:1]([C:3]1([CH2:23][C:24]([O:26]C)=[O:25])[C:8]2[NH:9][C:10]3[C:15]([C:7]=2[CH2:6][CH2:5][O:4]1)=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=3[O:17][CH2:18][C:19]([F:22])([F:21])[F:20])[CH3:2].O>CO>[CH2:1]([C:3]1([CH2:23][C:24]([OH:26])=[O:25])[C:8]2[NH:9][C:10]3[C:15]([C:7]=2[CH2:6][CH2:5][O:4]1)=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=3[O:17][CH2:18][C:19]([F:21])([F:20])[F:22])[CH3:2]

Participants

4

Reactant 2

HCID 962WaterHCID 131715880HCID 131715880, compound

Product 1

HCID 21272031HCID 21272031, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture consisting of 4-methyl-7-(2,2,2-trifluoroethoxy)tryptophol (9.8 g, 0.036 mol), methyl 3-methoxy-2-pentenoate (5.0 g, 0.035 mol), CH2Cl2 (400 mL) and BF3.Et2O (1 mL) was stirred at room temperature for 3 hours, washed with 5% NaHCO3, water, dried (MgSO4) and concentrated to afford 12 g of crude 1-ethyl-1,3,4,9-tetrahydro-5-methyl-8-(2,2,2-trifluoroethoxy)-pyrano[3,4-b]indole-1-acetic acid, methyl ester. Flash chromatography using 13% EtOAc-hexane gave 7.2 g of solid ester, mp 138°-140° C. The above ester was hydrolyzed in 400 mL MeOH containing 7.0 g KOH and 10 mL water by refluxing for 4 hours. The reaction solution was concentrated, diluted with water and extracted with ether (2×200 mL). The aqueous phase was acidified with 6N HCl and extracted with chloroform (2×200 mL). The combined chloroform extracts were washed with water, dried (MgSO4) and concentrated to afford 6.4 g of solid 1-ethyl-1,3,4,9-tetrahydro-5-methyl-8-(2,2,2-trifluoroethoxy)-pyrano[3,4-b]indole-1-acetic acid. Recrystallization from toluene-petroleum ether afforded 5.0 g (37%) of pure product, m.p. 149°-151° C.

Workup

  1. concentrationThe reaction solution was concentrated
  2. additiondiluted with water
  3. extractionextracted with ether (2×200 mL)
  4. extractionextracted with chloroform (2×200 mL)
  5. washThe combined chloroform extracts were washed with water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ff872d87be4c4f8585113629c75484f4
Source dataset
uspto-grants-1989_03
Patent number
US04810699

Reaction notes

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