Water → HCID 66938994, compound

HRID 1257395Notes

Reaction equation

HRID 1257395 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[N:10]=[C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)[S:12][C:13]=1[CH:14]=[O:15].[BH4-].[Na+].O>O1CCCC1.C(O)C>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[N:10]=[C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:23])[F:24])[CH:17]=2)[S:12][C:13]=1[CH2:14][OH:15]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86650592HCID 86650592, compound

Product 1

HCID 66938994HCID 66938994, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a mixed solution of the compound (2.2 g, 5.9 mmol) obtained in Example 89b in tetrahydrofuran/ethanol (v/v=1/1, 10 mL) was added sodium tetrahydroborate (340 mg, 8.9 mmol), and the mixture was stirred at 0° C. for 5 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=50/50) to give the title compound (2.0 g, 92%) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=50/50)

Sources & evidence

ORD record
ord-d8c2aa5b86d241b188a668134c9d5bb1
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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