Hydrochloric Acid → 2-(1H-tetrazol-1-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-5-carboxylic acid

HRID 2173368Notes

Reaction equation

HRID 2173368 reaction equation
[N:1]1([C:6]2[N:11]=[C:10]3[CH2:12][CH2:13][CH:14]([C:15]([O:17]C)=[O:16])[C:9]3=[CH:8][CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1.[OH-].[Li+].Cl>C1COCC1.O>[N:1]1([C:6]2[N:11]=[C:10]3[CH2:12][CH2:13][CH:14]([C:15]([OH:17])=[O:16])[C:9]3=[CH:8][CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 77230641methyl 2-(1H-tetrazol-1-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-5-carboxylate

Product 1

HCID 675172942-(1H-tetrazol-1-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 2-(1H-tetrazol-1-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-5-carboxylate (460 mg, 1.9 mmol) in THF (6 mL) was added lithium hydroxide (1.0 N aq. 3.8 mL, 3.8 mmol). The mixture was allowed to stir at 0° C. for 2 hours. LC at that point showed complete reaction. The reaction was diluted with water (10 mL). The pH was carefully adjusted to about 5 with 1N HCl. The solution was then extracted with EtOAc (30 mL×3). The extractions were combined, dried over sodium sulfate, and concentrated to furnish the title compound. LC-MS (IE, m/z): 231 [M+1]+; 1H-NMR (500 MHz, CD3OD) δ ppm 9.87 (s, 1H), 8.09 (d, J=8.0 Hz, 1H), 7.90 (d, J=8.0 Hz, 1H), 4.20 (t, J=8.0 Hz, 1H), 3.15 (m, 1H), 3.08 (m, 1H), 2.51 (m, 2H).

Workup

  1. customreaction
  2. extractionThe solution was then extracted with EtOAc (30 mL×3)
  3. extractionThe extractions
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2387743450954be58988f3a380fe6367
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

Loading…