Methanol → HCID 178491041, compound

HRID 582137Notes

Reaction equation

HRID 582137 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 3.4M 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-28d7ac94942742cface0c2118277d603
Source dataset
uspto-grants-1999_07
Patent number
US05922751

Reaction notes

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