HCID 21097831, compound → HCID 22932161, compound

HRID 1351103Notes

Reaction equation

HRID 1351103 reaction equation
C([O:8][C:9]1[C:13]([CH:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22]CC2C=CC=CC=2)O)=[C:12]([CH:30]([CH3:32])[CH3:31])[N:11]([CH2:33][CH2:34][OH:35])[N:10]=1)C1C=CC=CC=1>CO.[C].[Pd]>[OH:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[CH2:14][C:13]1[C:9](=[O:8])[NH:10][N:11]([CH2:33][CH2:34][OH:35])[C:12]=1[CH:30]([CH3:32])[CH3:31]

Participants

4

Reactant 1

HCID 21097831HCID 21097831, compound

Product 1

HCID 22932161HCID 22932161, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-benzyloxybromobenzene (1.66 g) in tetrahydrofuran (50 mL) was added tert-butyllithium (1.6 mol/L pentane solution, 4.33 mL) at −78° C. under an argon atmosphere, and the mixture was stirred for 5 minutes. To the reaction mixture was added a solution of 1-(2-benzoyloxyethyl)-3-benzyloxy-4-formyl-5-isopropyl-1H-pyrazole (620 mg) in tetrahydrofuran (5 mL), and the mixture was stirred at 0° C. for 30 minutes. To the reaction mixture was added a saturated aqueous ammonium chloride solution, and the resulting mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/1–2/1) to give 2-{3-benzyloxy-4-[(2-benzyloxyphenyl)hydroxymethyl]-5-isopropylpyrazol-1-yl}ethanol (448 mg). To a solution of 2-{3-benzyloxy-4-[(2-benzyloxyphenyl)hydroxymethyl]-5-isopropylpyrazol-1-yl}ethanol (448 mg) in methanol (5 mL) was added 10% palladium-carbon powder (448 mg), and the mixture was stirred at room temperature under a hydrogen atmosphere for 3 hours. The insoluble material was removed by filtration, and the solvent of the filtrate was removed under reduced pressure to give the title compound (220 mg).

Workup

  1. customThe insoluble material was removed by filtration
  2. customthe solvent of the filtrate was removed under reduced pressure

Sources & evidence

ORD record
ord-fc7b247d37c7468b8d1a4984a15c8a72
Source dataset
uspto-grants-2007_05
Patent number
US07217697B2

Reaction notes

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