Methanol → 2-(7-Fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid

HRID 1436210Notes

Reaction equation

HRID 1436210 reaction equation
C([O:3][C:4](=[O:19])[CH2:5][CH:6]1[C:10]2[NH:11][C:12]3[CH:13]=[CH:14][C:15]([F:18])=[CH:16][C:17]=3[C:9]=2[CH2:8][CH2:7]1)C.CO.[OH-].[Na+].C(OCC)(=O)C>O1CCCC1>[F:18][C:15]1[CH:14]=[CH:13][C:12]2[NH:11][C:10]3[CH:6]([CH2:5][C:4]([OH:19])=[O:3])[CH2:7][CH2:8][C:9]=3[C:17]=2[CH:16]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 11276987Ethyl 2-(7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate

Product 1

HCID 161093702-(7-Fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.24 g of the ester from Step 1 in 14 mL of tetrahydrofuran (THF) at room temperature, 7 mL of MeOH followed by 7 mL of 2N NaOH were added. After 2.5 h, the reaction mixture was poured into a separatory funnel containing ethyl acetate (EtOAc)/1N HCl. The phases were separated and the acidic phase was extracted twice with EtOAc. The organic layers were combined, washed with brine, dried over anhydrous Na2SO4 and evaporated to dryness to yield 1.08 g of a crude and unstable waxy brown oil that was used as such in the next step (>90% purity).

Workup

  1. customat room temperature
  2. additionwere added
  3. additionthe reaction mixture was poured into a separatory funnel
  4. customThe phases were separated
  5. extractionthe acidic phase was extracted twice with EtOAc
  6. washwashed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. customevaporated to dryness
  9. customto yield 1.08 g of a crude and unstable waxy brown oil that

Sources & evidence

ORD record
ord-4d737b2b586946f5869b660a65b1f4df
Source dataset
uspto-grants-2009_11
Patent number
US07618994B2

Reaction notes

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