Lithium Hydroxide → 3-(1H-tetrazol-1-yl)-6,7-dihydro-5H-cyclopenta[c]pyridine-7-carboxylic acid

HRID 2175916Notes

Reaction equation

HRID 2175916 reaction equation
[N:1]1([C:6]2[N:11]=[CH:10][C:9]3[CH:12]([C:15]([O-:17])=[O:16])[CH2:13][CH2:14][C:8]=3[CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1.[OH-].[Li+]>O1CCCC1.O>[N:1]1([C:6]2[N:11]=[CH:10][C:9]3[CH:12]([C:15]([OH:17])=[O:16])[CH2:13][CH2:14][C:8]=3[CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 866930243-(1H-tetrazol-1-yl)-6,7-dihydro-5H-cyclopenta[c]pyridine-7-carboxylate

Product 1

HCID 675172303-(1H-tetrazol-1-yl)-6,7-dihydro-5H-cyclopenta[c]pyridine-7-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(1H-tetrazol-1-yl)-6,7-dihydro-5H-cyclopenta[c]pyridine-7-carboxylate (235 mg, 0.958 mmol) in tetrahydrofuran (5 mL) and water (1.5 mL) at room temperature was treated with lithium hydroxide solution (1 M, 1.44 mL). After 30 min. the solution was concentrated to remove tetrahydrofuran and the remaining aqueous acidified with 1 N hydrochloric acid solution (to pH˜4) and extracted with ethyl acetate (3×). The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated to provide the title compound: 1H NMR (500 MHz, CD3OD), δ 9.89 (s, 1H), 8.58 (s, 1H), 8.01 (s, 1H), 4.25 (dd, J=5.0, 5.0 Hz, 1H), 3.27-3.05 (m, 2H), 2.47-2.57 (m, 2H); LC/MS (M+1)+=232.2.

Workup

  1. concentrationAfter 30 min. the solution was concentrated
  2. customto remove tetrahydrofuran
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined organics were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1304575dcc824a87957d4333a5eb992f
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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