Sodium Hydroxide → 2,4,5,6,7,8-Hexahydro-cycloheptapyrazole-3-carboxylic acid

HRID 1366879Notes

Reaction equation

HRID 1366879 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[C:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:11]=2[NH:10][N:9]=1)=[O:7])C>CO>[NH:10]1[C:11]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:12]=2[C:8]([C:6]([OH:7])=[O:5])=[N:9]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20094653HCID 20094653, compound

Product 1

HCID 6553432,4,5,6,7,8-Hexahydro-cycloheptapyrazole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Freshly prepared aq. NaOH (10 M in H2O, 9.66 mmol) was added to a stirring, room temperature solution of 14 (0.4029 g, 1.93 mmol) in MeOH (4.8 mL, 0.4 M) under N2. The reaction was then heated to reflux until the reaction was judged complete by TLC (0.5 h): The reaction was concentrated and then dissolved in 3.8 mL H2O. 10% aq. HCl was added dropwise until the pH=2. The white solid that precipitated from the reaction was filtered off and washed with cold H2O. The solid was dried under vacuum overnight to obtain 15. Note: An undesired impurity that does not crash out of solution upon HCl addition has a retention time of 8.708 min by HPLC. 1H (CD3OD, 400 MHz): δ 2.98-2.90 (2H, m), 2.80-2.72 (2H, m), 1.92-1.82 (2H, m), 1.70-1.58 (4H, m) ppm. 13C (CD3OD, 100 MHz): δ 164.81, 151.31, 136.87, 125.13, 33.36, 29.73, 28.78, 28.49, 25.17 ppm. DEPT (CD3OD, 100 MHz): CH2 carbons: 33.36, 29.73, 28.78, 28.49, 25.17 ppm. HPLC: 7.545 min.

Workup

  1. temperatureThe reaction was then heated
  2. temperatureto reflux until the reaction
  3. customwas judged complete by TLC (0.5 h)
  4. concentrationThe reaction was concentrated
  5. dissolutiondissolved in 3.8 mL H2O
  6. addition10% aq. HCl was added dropwise until the pH=2
  7. customThe white solid that precipitated from the reaction
  8. filtrationwas filtered off
  9. washwashed with cold H2O
  10. customThe solid was dried under vacuum overnight

Sources & evidence

ORD record
ord-b766389346274911b73f0aa7b8642485
Source dataset
uspto-grants-2011_02
Patent number
US07893098B2

Reaction notes

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