Sodium borohydride → 5-(3-Butyl-5-hydroxymethyl-isoxazol-4-ylmethoxy)-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester

HRID 1695456Notes

Reaction equation

HRID 1695456 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:23])[N:7]=[C:8]([O:10][CH2:11][C:12]2[C:13]([CH2:19][CH2:20][CH2:21][CH3:22])=[N:14][O:15][C:16]=2[CH:17]=[O:18])[CH:9]=1)=[O:4].[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:23])[N:7]=[C:8]([O:10][CH2:11][C:12]2[C:13]([CH2:19][CH2:20][CH2:21][CH3:22])=[N:14][O:15][C:16]=2[CH2:17][OH:18])[CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 866472775-(3-butyl-5-formyl-isoxazol-4-ylmethoxy)-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester

Product 1

HCID 666437015-(3-Butyl-5-hydroxymethyl-isoxazol-4-ylmethoxy)-2-methyl-2H-pyrazole-3-carboxylic acid methyl esterYield 46%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-(3-butyl-5-formyl-isoxazol-4-ylmethoxy)-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (80 mg, 0.25 mmol) in methanol (4 mL) was added sodium borohydride (18.8 mg, 0.5 mmol) in portions over 3 min. Upon addition, the reaction became a clear light yellow solution containing a black precipitate. After stirring at room temperature for 1.5 h, the mixture was filtered over Celite® and the filter cake was washed with methanol. The filtrate was concentrated and the residue was portioned between 0.5M aqueous hydrochloric acid and ethyl acetate. The aqueous phase was extracted two times with ethyl acetate and the combined organic phases were washed with brine, dried over sodium sulfate and concentrated to a yellow oil. The crude material was purified by chromatography (silica, heptane:acetone 7.5:2.5) to afford the title compound (37 mg, 46%) as a dark brown oil. MS: m/e=324.3 [M+H]+.

Workup

  1. additionUpon addition
  2. additioncontaining a black precipitate
  3. filtrationthe mixture was filtered over Celite®
  4. washthe filter cake was washed with methanol
  5. concentrationThe filtrate was concentrated
  6. extractionThe aqueous phase was extracted two times with ethyl acetate
  7. washthe combined organic phases were washed with brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated to a yellow oil
  10. customThe crude material was purified by chromatography (silica, heptane:acetone 7.5:2.5)

Sources & evidence

ORD record
ord-ffa53c63a61744c5b1d3a7ccecbaefc9
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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