Water → (4-Methoxy-indan-5-yl)-pyrrolidin-1-yl-methanone

HRID 1099376Notes

Reaction equation

HRID 1099376 reaction equation
[CH3:1][O:2][C:3]1[C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][CH2:7]2.[C:15]([C:22]1[NH:23][CH:24]=[CH:25]N=1)(C1NC=CN=1)=O.N1CCCC1.O>O1CCCC1>[CH3:1][O:2][C:3]1[C:11]([C:12]([N:23]2[CH2:22][CH2:15][CH2:25][CH2:24]2)=[O:14])=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][CH2:7]2

Participants

6

Reactant 4

HCID 962WaterHCID 31268PyrrolidineHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 668121244-Methoxy-indan-5-carboxylic acid

Product 1

HCID 66813030(4-Methoxy-indan-5-yl)-pyrrolidin-1-yl-methanoneYield 39.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
67.5 °C

Procedure

To a clear solution of 4-Methoxy-indan-5-carboxylic acid (12.0 gm, 0.0625 mole) in Tetrahydrofuran (60 ml), Carbonyl-diimidazole (13.24 gm, 0.0812 mole) was added at 25-28° C. The reaction mixture was heated to 65-70° C. and stirred for 2 hours to the reaction mixture, a solution of Pyrrolidine (5.74 ml, 0.0687 mole) in Tetrahydrofuran (20 ml) was added at 10-15° C. The reaction mixture was poured into water (200 ml) and extracted with Ethylacetate (2×100 ml). The organic layer was dried over Sodium sulphate, distilled under vacuum and purified by column chromatography using Ethyl acetate:Hexane (20:80) as mobile phase. The fractions were distilled under vacuum to give 6.0 gm of desired product as a viscous oil.

Workup

  1. extractionextracted with Ethylacetate (2×100 ml)
  2. dry with materialThe organic layer was dried over Sodium sulphate
  3. distillationdistilled under vacuum
  4. custompurified by column chromatography
  5. distillationThe fractions were distilled under vacuum

Sources & evidence

ORD record
ord-8cb75a5f962c4be6b39345b2fc9c096b
Source dataset
uspto-grants-2012_03
Patent number
US08143424B2

Reaction notes

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