Acetone → HCID 21934880, compound

HRID 1241515Notes

Reaction equation

HRID 1241515 reaction equation
C[O:2][C:3]1(OC)[CH2:6][CH:5]([CH2:7][N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:4]1.CC(C)=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[N:8]1([CH2:7][CH:5]2[CH2:4][C:3](=[O:2])[CH2:6]2)[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 521998p-Toluenesulfonic acid monohydrateHCID 21934883HCID 21934883, compound2×

Product 1

HCID 21934880HCID 21934880, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirring solution of 1-[(3,3-dimethoxy-cyclobutyl)methyl]-pyrrolidine (intermediate 5, general prcedure B, step B) (1.6 g, 8.0 mmol) in 3:1 acetone:H2O (100 mL) was added p-toluenesulfonic acid mono hydrate (1.5 g, 8.0 mmol). The reaction mixture was heated to 65 C for 1 hour. Both TLC and GS/MS analysis indicated complete consumption of starting material. The reaction was cooled to room temperature and then the acetone was removed under reduced pressure. The resulting mixture was diluted with CH2Cl2 and washed with an aqueous solution of NaHCO3. The aqueous layer was back extracted with 3:1 CHCl3:iso-propyl alcohol. The combined organic layers were dried over magnesium sulfate, filtered through a fritted funnel and then concentrated under reduced pressure to yield the title compound (0.94 g, 76% yield) as a colorless oil. This material was processed without further purification.

Workup

  1. temperatureThe reaction mixture was heated to 65 C for 1 hour
  2. customconsumption of starting material
  3. customthe acetone was removed under reduced pressure
  4. additionThe resulting mixture was diluted with CH2Cl2
  5. washwashed with an aqueous solution of NaHCO3
  6. extractionThe aqueous layer was back extracted with 3:1 CHCl3
  7. dry with materialThe combined organic layers were dried over magnesium sulfate
  8. filtrationfiltered through a fritted funnel
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8154cde787cb42fb8e201f9c37938700
Source dataset
uspto-grants-2006_10
Patent number
US07115600B2

Reaction notes

Loading…