Triethylamine → (+)-(1S,2S)-3-formyl-2-methyl-8-(2-hydroxy-2,3-dihydro-1-indenyloxy)-imidazo[1,2-a]pyridine

HRID 1195733Notes

Reaction equation

HRID 1195733 reaction equation
[CH:1]([C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[C:11]([OH:12])[C:6]2=[N:5][C:4]=1[CH3:13])=[O:2].C(N([CH2:19][CH3:20])CC)C>CO>[CH:1]([C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[C:11]([O:12][C@H:10]3[C:19]4[C:20](=[CH:1][CH:3]=[CH:4][CH:13]=4)[CH2:6][C@@H:11]3[OH:12])[C:6]2=[N:5][C:4]=1[CH3:13])=[O:2]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 232941873-Formyl-8-hydroxy-2-methylimidazo[1,2-a]pyridine

Product 1

HCID 57075834(+)-(1S,2S)-3-formyl-2-methyl-8-(2-hydroxy-2,3-dihydro-1-indenyloxy)-imidazo[1,2-a]pyridineYield 52.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.30 g of 3-formyl-8-hydroxy-2-methyl-imidazo[1,2-a]pyridine and 1.40 g (-)-1R,2S-indenoxide are reacted, analogously to the method described in Example 21, with 1.90 g of triethylamine in 425 ml of aqueous methanol (350 ml methanol+75 g water) at 50° C. After 8 hours the solution is evaporated and the residue dissolved in 150 ml water. 4 g of sodium carbonate is added and extracted with 4×100 ml ethyl acetate. The organic phases are washed with 2×200 ml sodium carbonate solution and 4×200 ml water, dried over magnesium sulfate and evaporated. The solid residue is mixed in 100 ml cyclohexane filtered and dried. 1.51 g of the title compound m.p. 187°- 192° C. is isolated [α]D22 =+112° (c=0.5, chloroform).

Workup

  1. customAfter 8 hours the solution is evaporated
  2. dissolutionthe residue dissolved in 150 ml water
  3. addition4 g of sodium carbonate is added
  4. extractionextracted with 4×100 ml ethyl acetate
  5. washThe organic phases are washed with 2×200 ml sodium carbonate solution and 4×200 ml water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. additionThe solid residue is mixed in 100 ml cyclohexane
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-8ce39acaa1fa4723b0396a935257b641
Source dataset
uspto-grants-1992_05
Patent number
US05112834

Reaction notes

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