Sodium Hydroxide → HCID 58495484, compound

HRID 1190984Notes

Reaction equation

HRID 1190984 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1([CH3:23])[CH2:13][CH2:12][CH2:11][CH:10]([O:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]#[N:22])=[N:19][CH:20]=2)[CH2:9]1.[OH-].[Na+]>C1COCC1.O.C(OCC)C>[NH2:22][CH2:21][C:18]1[CH:17]=[CH:16][C:15]([O:14][CH:10]2[CH2:11][CH2:12][CH2:13][C:8]([CH3:23])([CH3:7])[CH2:9]2)=[CH:20][N:19]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 58495682HCID 58495682, compound

Product 1

HCID 58495484HCID 58495484, compoundYield 88.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, add lithium aluminum hydride (264 mg, 6.95 mmol) to THF (15 mL) at 0° C. Add a solution of 5-(3,3-dimethylcyclohexyloxy)-pyridine-2-carbonitrile (0.4 g, 1.74 mmol) in THF (5 mL), stir at 0° C. for 1 h and warm to room temperature overnight. Cool the mixture at 0° C. and carefully add water (0.3 mL). Add diethyl ether (25 mL), 3N aqueous NaOH (0.3 mL) and water (0.9 mL), and stir for 1 h at room temperature. Filter the solid residue and concentrate the filtrate in vacuo to obtain the title compound as a colorless oil (360 mg, 88%). MS (APCI+) m/z: 235 (M+H)+.

Workup

  1. temperaturewarm to room temperature overnight
  2. temperatureCool the mixture at 0° C.
  3. filtrationFilter the solid residue
  4. concentrationconcentrate the filtrate in vacuo

Sources & evidence

ORD record
ord-d5c99ba9c23344a8bb615dc97b7ffec2
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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