Water → (1S,2S)-2-pyridin-2-ylcyclopropane-1-carboxylic acid

HRID 1774004Notes

Reaction equation

HRID 1774004 reaction equation
CON(C)[C:4]([C@@H:6]1[CH2:8][C@H:7]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)=[O:5].CC(C)([O-:19])C.[K+].O>CCOCC>[N:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C@@H:7]1[CH2:8][C@H:6]1[C:4]([OH:19])=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 23665647Potassium tert-butoxide2×HCID 131734716HCID 131734716, compound

Product 1

HCID 39235822(1S,2S)-2-pyridin-2-ylcyclopropane-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of (±)-(trans)-2-pyridin-2-yl-cyclopropanecarboxylic acid methoxy-methyl-amide (950 mg, 4.61 mmol, 1 eq) in Et2O (30 mL), potassium tert-butoxide (569 mg, 5.07 mmol, 1.1 eq) and H2O (0.4 mL) were added. The mixture was stirred at r.t. for 18 hours. Potassium tert-butoxide (1.86 g, 16.6 mmol, 3.6 eq.) was added again. The mixture was stirred at r.t. for 24 hours. The reaction mixture was concentrated in vacuo. The residue was dissolved in water (5 mL) and formic acid (3 mL). The solution was directly purified by prep. HPLC (column: Atlantis, 30×75 mm, 10 um, UV/MS, acidic conditions, extremely polar method) and concentrated in vacuo to give the title compound as a white solid.

Workup

  1. stirringThe mixture was stirred at r.t. for 24 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in water (5 mL)
  4. customThe solution was directly purified by prep
  5. concentrationHPLC (column: Atlantis, 30×75 mm, 10 um, UV/MS, acidic conditions, extremely polar method) and concentrated in vacuo

Sources & evidence

ORD record
ord-eccd35fc471c470b80d0a99d7eb806b7
Source dataset
uspto-grants-2016_02
Patent number
US09255090B2

Reaction notes

Loading…