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

HRID 1195732Notes

Reaction equation

HRID 1195732 reaction equation
[C:1]([CH2:3][C:4]1[N:8]2[CH:9]=[CH:10][CH:11]=[C:12]([OH:13])[C:7]2=[N:6][C:5]=1[CH3:14])#[N:2].C(N([CH2:20][CH3:21])CC)C>CO>[C:1]([CH2:3][C:4]1[N:8]2[CH:9]=[CH:10][CH:11]=[C:12]([O:13][C@H:11]3[C:20]4[C:21](=[CH:1][CH:3]=[CH:4][CH:5]=4)[CH2:7][C@@H:12]3[OH:13])[C:7]2=[N:6][C:5]=1[CH3:14])#[N:2]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 133382662-(8-Hydroxy-2-methylimidazo[1,2-a]pyridin-3-yl)acetonitrile

Product 1

HCID 57177844(+)-(1S,2S)-3-cyanomethyl-2-methyl-8-(2-hydroxy-2,3-dihydro-1-indenyloxy)-imidazo[1,2-a]pyridineYield 18.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

750 mg 3-cyanomethyl-8-hydroxy-2-methyl-imidazo[1,2-a]pyridine are reacted, analogously to the method described in Example 21, with 210 mg (-)-1R,2S-indenoxide and 400 mg triethylamine in aqueous methanol (60 ml methanol+15 ml water) at room temperature. After 3 days the solution is evaporated and the residue taken up in 50 ml water. The precipitate is filtered off and purified by chromatography over silica gel (mobile phase: ethyl acetate/methanol=10:1). After evaporation the residue is precipitated from methylene chloride/cyclohexane. 120 mg of the title compound is isolated. [α]D22 =+113° (c=1, chloroform).

Workup

  1. customAfter 3 days the solution is evaporated
  2. filtrationThe precipitate is filtered off
  3. custompurified by chromatography over silica gel (mobile phase: ethyl acetate/methanol=10:1)
  4. customAfter evaporation the residue
  5. customis precipitated from methylene chloride/cyclohexane

Sources & evidence

ORD record
ord-28c66c3dd97845ce994292e1d58f6e94
Source dataset
uspto-grants-1992_05
Patent number
US05112834

Reaction notes

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