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

HRID 2250533Notes

Reaction equation

HRID 2250533 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+]>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

5

Reactant 3

HCID 887MethanolHCID 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 acetaqte (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. additioncontaining ethyl acetaqte (EtOAc)/1N HCl
  5. customThe phases were separated
  6. extractionthe acidic phase was extracted twice with EtOAc
  7. washwashed with brine
  8. dry with materialdried over anhydrous Na2SO4
  9. customevaporated to dryness
  10. customto yield 1.08 g of a crude and unstable waxy brown oil that

Sources & evidence

ORD record
ord-e60c00b8b4cd499a9e31ed1248a3701e
Source dataset
uspto-grants-2008_01
Patent number
US07317036B2

Reaction notes

Loading…