Sodium borohydride → HCID 24782884, compound

HRID 1685806Notes

Reaction equation

HRID 1685806 reaction equation
[O:1]=[C:2]1[CH2:6][S:5][CH2:4][CH:3]1[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:18])[C:15]([OH:17])=[O:16])=[CH:10][CH:9]=1.[BH4-].[Na+]>C(O)C>[OH:1][CH:2]1[CH2:6][S:5][CH2:4][CH:3]1[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:18])[C:15]([OH:17])=[O:16])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 24782883HCID 24782883, compound

Product 1

HCID 24782884HCID 24782884, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-[4-(4-Oxothiolan-3-ylmethyl)phenyl]propionic acid (24 mg) obtained in Example 8 was dissolved in ethanol (1.0 ml), sodium borohydride (9.4 mg) was added stirring on an ice bath, and stirred for 1 hour. The reaction mixture was quenched with 2.0 M aqueous hydrochloric acid, and extracted with ethyl acetate. The aqueous layer was extracted again with ethyl acetate, and the organic layers were combined, and washed with saturated brine. The organic layer was dried over magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate/acetic acid=50/50/1) to give the compounds of Example 9-A (colorless crystals, 4.6 mg, 19%) and Example 9-B (colorless oil, 11.6 mg, 48%).

Workup

  1. stirringstirred for 1 hour
  2. customThe reaction mixture was quenched with 2.0 M aqueous hydrochloric acid
  3. extractionextracted with ethyl acetate
  4. extractionThe aqueous layer was extracted again with ethyl acetate
  5. washwashed with saturated brine
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate/acetic acid=50/50/1)

Sources & evidence

ORD record
ord-b0120bdd123949ecb009b2c65aa75adf
Source dataset
uspto-grants-2012_04
Patent number
US08148421B2

Reaction notes

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