Nitrogen → 5-(2-Methyl-[1,3]dioxolan-2-yl)-pentanoic acid

HRID 1189357Notes

Reaction equation

HRID 1189357 reaction equation
N#N.C[O:4][C:5](=[O:16])[CH2:6][CH2:7][CH2:8][CH2:9][C:10]1([CH3:15])[O:14][CH2:13][CH2:12][O:11]1.O.[OH-].[Li+]>C1COCC1.O>[CH3:15][C:10]1([CH2:9][CH2:8][CH2:7][CH2:6][C:5]([OH:16])=[O:4])[O:14][CH2:13][CH2:12][O:11]1

Participants

6

Reactant 3

HCID 947NitrogenHCID 168937Lithium hydroxide, monohydrateHCID 11063488Methyl 5-(2-methyl-1,3-dioxolan-2-yl)pentanoate

Product 1

HCID 154537565-(2-Methyl-[1,3]dioxolan-2-yl)-pentanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 5-(2-methyl-[1,3]dioxolan-2-yl)-pentanoic acid methyl ester (5.43 g, 26.85 mmol) in a mixture of THF (70 mL) and water (70 mL) was treated at rt with lithium hydroxide monohydrate (1.45 g, 34.55 mmol) and the mixture was stirred for 3 h at rt. The THF was removed under reduced pressure and the aqueous phase was washed with EA, concentrated under reduced pressure and poured in cold sat. aq. NH4Cl. The pH was adjusted to 4-5 using 1N HCl and the aqueous phase was extracted with EA (3×). The combined org. extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (20:1→1:2 hept-EA) gave the title compound as a white solid. LC-MS-conditions 02: tR=0.68 min [M+H]+=189.52.

Workup

  1. customThe THF was removed under reduced pressure
  2. washthe aqueous phase was washed with EA
  3. concentrationconcentrated under reduced pressure
  4. additionpoured in cold sat. aq. NH4Cl
  5. extractionthe aqueous phase was extracted with EA (3×)
  6. dry with materialextracts were dried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure
  9. customPurification of the residue by FC (20:1→1:2 hept-EA)

Sources & evidence

ORD record
ord-3b39d1677158414c92ba1c38d23f3baa
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

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