Water → HCID 66939196, compound

HRID 1257399Notes

Reaction equation

HRID 1257399 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[C:9]([CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=2)[CH:10]=[O:11])=[N:4][C:3]=1[CH2:19][O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1.[BH4-].[Na+].O>O1CCCC1.C(O)C>[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[C:9]([CH2:10][OH:11])[CH:12]=[C:13]([C:15]([F:17])([F:18])[F:16])[CH:14]=2)=[N:4][C:3]=1[CH2:19][O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86650593HCID 86650593, compound

Product 1

HCID 66939196HCID 66939196, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a mixed solution of the compound (1.6 g, 4.1 mmol) obtained in Example 95b in tetrahydrofuran/ethanol (v/v=1/1, 8 mL) was added sodium tetrahydroborate (230 mg, 6.1 mmol), and the mixture was stirred overnight while allowing to spontaneously warm to room temperature from 0° C. 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=65/35) to give the title compound (1.3 g, 84%) as a pale-orange 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=65/35)

Sources & evidence

ORD record
ord-03092593645a429491d8140c904ea0fe
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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