Pyrrolidine → HCID 22274645, compound

HRID 1064688Notes

Reaction equation

HRID 1064688 reaction equation
Br[CH2:2][CH2:3][C:4]1[C:5](=[O:16])[O:6][C:7]2[C:12]([C:13]=1[CH3:14])=[CH:11][C:10]([OH:15])=[CH:9][CH:8]=2.[NH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1>CN(C=O)C.O>[OH:15][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[O:6][C:5](=[O:16])[C:4]([CH2:3][CH2:2][N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)=[C:13]2[CH3:14]

Participants

5

Reactant 2

HCID 31268PyrrolidineHCID 22274543HCID 22274543, compound

Product 1

HCID 22274645HCID 22274645, compoundYield 250.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of Example 41A (0.20 g, 0.70 mmol) and pyrrolidine (0.50 mL, 6.0 mmol) in DMF (2 mL) was heated to 75° C. for 16 hours, cooled to ambient temperature, diluted with water (20 mL) and extracted with ethyl acetate (3×50 mL). The combined ethyl acetate was dried (MgSO4), filtered, concentrated under reduced pressure and chromatographed on silica with 10% methanol in dichloromethane to give the titled compound (0.48 g, 25%). MS (DCI) m/z 274 (M+H)+;

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. dry with materialThe combined ethyl acetate was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customchromatographed on silica with 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-d7249a1971cf42b486ba573ced94bb67
Source dataset
uspto-grants-2005_11
Patent number
US06969730B2

Reaction notes

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