Sodium borohydride → HCID 66718163, compound

HRID 1514741Notes

Reaction equation

HRID 1514741 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([CH2:27][CH2:28][CH2:29][CH3:30])=[N:14][O:15][C:16]=2[CH:17]([OH:26])C(O)C2C=CC=CC=2)=[N:6][CH:5]=1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4].[BH4-].[Na+]>C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([CH2:27][CH2:28][CH2:29][CH3:30])=[N:14][O:15][C:16]=2[CH2:17][OH:26])=[N:6][CH:5]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 66718222HCID 66718222, compoundHCID 178418268HCID 178418268, compound

Product 1

HCID 66718163HCID 66718163, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of 6-[3-butyl-5-(1,2-dihydroxy-2-phenylethyl)-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester (890 mg, 2.09 mmol) in benzene (10 mL) was added lead tetraacetate (1.39 g, 3.13 mmol) with benzene (5 mL) and the reaction was stirred at room temperature for 45 min. The suspension was filtered over celite and the filtrate was concentrated to a yellow oil. The oil was taken up in methanol (20 mL) and sodium borohydride (198 mg, 5.24 mmol) was added 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 15 min, 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:ethyl acetate 1:0 to 1:1) to afford the title compound (495 mg, 68%) as a colorless oil. MS: m/e=321.2 [M+H]+.

Workup

  1. filtrationThe suspension was filtered over celite
  2. concentrationthe filtrate was concentrated to a yellow oil
  3. additionUpon addition
  4. additioncontaining a black precipitate
  5. stirringAfter stirring at room temperature for 15 min
  6. filtrationthe mixture was filtered over celite
  7. washthe filter cake was washed with methanol
  8. concentrationThe filtrate was concentrated
  9. extractionThe aqueous phase was extracted two times with ethyl acetate
  10. washthe combined organic phases were washed with brine
  11. dry with materialdried over sodium sulfate
  12. concentrationconcentrated to a yellow oil
  13. customThe crude material was purified by chromatography (silica, heptane:ethyl acetate 1:0 to 1:1)

Sources & evidence

ORD record
ord-e6bb012a96004e2cbd6d94935c7837c3
Source dataset
uspto-grants-2012_07
Patent number
US08222246B2

Reaction notes

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