Lithium borohydride → HCID 58305661, compound

HRID 2362246Notes

Reaction equation

HRID 2362246 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:11][CH:10]=[C:9]2[CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[CH:4][C:3]=1[C:24](OC)=[O:25].[Li+].[BH4-]>C1COCC1>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:11][CH:10]=[C:9]2[CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[CH:4][C:3]=1[CH2:24][OH:25]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 58305607HCID 58305607, compound

Product 1

HCID 58305661HCID 58305661, compoundYield 48.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(1-(4-hydroxy-3-(methoxycarbonyl)phenyl)-5-phenyl-1H-pyrrol-2-yl)propanoic acid (40 mg, 0.109 mmol) in 2 ml anhydrous THF was added LiBH4 (2M in THF, 0.14 ml, 2.5 eq.) via a syringe at 0° C. The reaction mixture was stirred at rt for 4 hours. Mixture was quenched with saturated sol. NH4Cl, then acidified to pH=2 using 10% HCl solution. This was extracted several times using ethyl acetate. Combined organic layers were washed with brine, dried (Na2SO4) and concentrated. The crude was purified by preparative TLC using 1:1 ethyl acetate/hexane. 18 mg of 3-(1-(4-hydroxy-3-(hydroxymethyl)phenyl)-5-phenyl-1H-pyrrol-2-yl)propanoic acid was obtained, 47% yield.

Workup

  1. customMixture was quenched with saturated sol. NH4Cl
  2. extractionThis was extracted several times
  3. washCombined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude was purified by preparative TLC

Sources & evidence

ORD record
ord-5b8b66a83a9d4d67bd0e7be1541dd5fb
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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