Potassium Carbonate → HCID 44818993, compound

HRID 1909696Notes

Reaction equation

HRID 1909696 reaction equation
Cl.[Cl:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][C:8]2[CH:20]=[CH:19][C:11]([O:12][CH2:13][C@H:14]3[CH2:18][CH2:17][CH2:16][NH:15]3)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.Br[CH2:24][CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH3:30][O:29][C:27](=[O:28])[CH2:26][CH2:25][CH2:24][N:15]1[CH2:16][CH2:17][CH2:18][C@@H:14]1[CH2:13][O:12][C:11]1[CH:19]=[CH:20][C:8]([CH2:7][C:6]2[CH:21]=[CH:22][C:3]([Cl:2])=[CH:4][CH:5]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 107604Methyl 4-bromobutyrateHCID 68997734HCID 68997734, compound

Product 1

HCID 44818993HCID 44818993, compoundYield 35.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of (R)-2-[4-(4-chloro-benzyl)-phenoxymethyl]-pyrrolidine hydrochloride (1.37 g, 4 mmol), methyl 4-bromobutyrate (916 mg, 5 mmol), and potassium carbonate (1.12 g, 8 mmol) in DMF (15 mL) was stirred for 60 h at rt. The solvent was removed in vacuo to obtain the crude mixture. The mixture was diluted with 30 mL of water and extracted with ethylacetate (130 mL). The aqueous layer was re-extracted with ethyl acetate (2×100 mL). The combined organic layers were dried over anhy. Na2SO4 and the solvent was removed in vacuo to obtain the crude mixture, which was purified by silica gel flash chromatography to obtain the title product (570 mg, 35%).

Workup

  1. customThe solvent was removed in vacuo
  2. customto obtain the crude mixture
  3. extractionextracted with ethylacetate (130 mL)
  4. extractionThe aqueous layer was re-extracted with ethyl acetate (2×100 mL)
  5. customThe combined organic layers were dried over anhy
  6. customNa2SO4 and the solvent was removed in vacuo
  7. customto obtain the crude mixture, which
  8. customwas purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-0812ec2f97884c0d8c96588de4a27ae0
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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