Water → HCID 15907518, compound

HRID 427756Notes

Reaction equation

HRID 427756 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][N:8]1[C:12]([NH:13][C:14](=O)[C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:11][C:10]([CH3:20])=[N:9]1.O.[OH-].[Na+]>C1COCC1>[CH3:16][C:15]([CH3:18])([CH3:17])[CH2:14][NH:13][C:12]1[N:8]([CH3:7])[N:9]=[C:10]([CH3:20])[CH:11]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 2818790HCID 2818790, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15907518HCID 15907518, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
67 °C

Procedure

To 4.7 g (123 mmol) of LiAlH4 in 150 mL of THF at 0° C. was added a solution of 12.0 g (61.45 mmol) of N-(2,5-dimethyl-2H-pyrazol-3-yl)-2,2-dimethyl-propionamide and 100 mL THF in drops over 60 min. After addition is complete, the reaction mixture was heated to 67° C. for 42 h. After cooling to 23° C., 5 mL H2O was carefully added, followed by 5 mL 5N NaOH and 5 mL H2O. The resulting mixture was filtered through Celite, evaporated to a yellow oil, dissolved in 300 mL EtOAc, washed with 1×100 mL brine, 1×100 mL H2O, 1×100 mL brine, dried over MgSO4, filtered and evaporated to give 9.45 g (52.1 mmol, an 85% yield) of the title compound as a light yellow oil. 1H NMR (300 MHz, CDCl3): δ0.98 (s, 9H), 2.17 (s, 3H), 2.81 (m, 2H), 3.56 (s, 3H), 5.24 (s, 1H); IR (KBr, cm−1): 3261m, 2956m, 2866m, 1568s, 1476m, 1367m, 1362m, 1267m, 1200m, 729m; MS (ES) m/z (relative intensity): 182 (M++H, 100).

Workup

  1. additionAfter addition
  2. temperatureAfter cooling to 23° C.
  3. filtrationThe resulting mixture was filtered through Celite
  4. customevaporated to a yellow oil
  5. dissolutiondissolved in 300 mL EtOAc
  6. washwashed with 1×100 mL brine, 1×100 mL H2O, 1×100 mL brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. customto give 9.45 g (52.1 mmol

Sources & evidence

ORD record
ord-d2e32aa8bb604022929485c339380e8e
Source dataset
uspto-grants-2001_11
Patent number
US06313149B1

Reaction notes

Loading…