Methanol → HCID 178491041, compound

HRID 1871536Notes

Reaction equation

HRID 1871536 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:22]=[CH:23][C:24]=2[O:25][CH3:26])[CH2:10][NH:11][C:12]2[C:16]([C:17](OCC)=O)=[CH:15][NH:14][N:13]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].COCCO[Al+]OCCOC.[Na+].[H-].CO>C1COCC1.C1(C)C=CC=CC=1.O>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:22]=[CH:23][C:24]=2[O:25][CH3:26])[CH2:10][NH:11][C:12]2[C:16]([CH3:17])=[CH:15][NH:14][N:13]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 3

HCID 887MethanolHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride2×HCID 178469931HCID 178469931, compound

Product 1

HCID 178491041HCID 178491041, compoundYield 38%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of ethyl 3-(3-cyclopentyloxy-4-methoxybenzylamino-pyrazole-4-carboxylate) (from EXAMPLE 12) (5.4 g, 0.015 mol) in THF (50 mL) at 0° was treated with sodium bis (2-methoxyethoxy)aluminum hydride (0.03 mole), 9 mL of 3.4 M solution in toluene. After 3 hours, another 9 mL portion of the sodium bis(2-methoxy-ethoxy)aluminum hydride solution (0.03 mol) was added. The reaction was stirred overnight at room temperature and methanol (20 mL) was added. The reaction mixture was diluted with water and extracted with ethyl acetate. The ethyl acetate extracts were washed with water and evaporated under reduced pressure. The residue crystallized upon trituration with hexanes. Pure title compound (1.7 g, 38%), mp 76-77°, was obtained after two crystallizations from methyl t-butylether.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate extracts were washed with water
  3. customevaporated under reduced pressure
  4. customThe residue crystallized upon trituration with hexanes

Sources & evidence

ORD record
ord-59c73757b5e34ff9a0402f00f8d9c6c0
Source dataset
uspto-grants-2000_08
Patent number
US06103749

Reaction notes

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