Methyl 3-bromobenzoate → HCID 66970375, compound

HRID 1361610Notes

Reaction equation

HRID 1361610 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:48][N:49]([CH3:55])[C@H:50]1[CH2:54][CH2:53][NH:52][CH2:51]1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:48][N:49]([CH3:55])[C@H:50]1[CH2:54][CH2:53][N:52]([C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])[CH2:51]1

Participants

7

Reactant 4

HCID 12070Methyl 3-bromobenzoateHCID 62657Potassium Phosphate, TribasicHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidine

Product 1

HCID 66970375HCID 66970375, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 3-bromobenzoate (1.0 g, 4.7 mmol), 2-(dicyclohexylphosphino)-2′-(N,N-dimethylamino)biphenyl (0.037 g, 0.093 mmol), tris(dibenzylidineacetone)dipalladium (0) (0.021 g, 0.023 mmol), anhydrous K3PO4 (1.4 g, 6.5 mmol) in 9.3 mL toluene under argon was added (S)-N,N-dimethylpyrrolidin-3-amine (0.71 mL, 5.6 mmol). The reaction was sealed and heated to 80 deg. C. for 3 days. The reaction was cooled to ambient temperature, was diluted with ethyl acetate, and filtered through celite. The filtrate was concentrated in vacuo to give a brown oil, which was further purified by silica gel chromatography, using 90/10/1 dichloromethane/methanol/sat'd ammonium hydroxide as eluent to give (S)-methyl 3-(3-(dimethylamino)pyrrolidin-1-yl)benzoate as a light brown oil.

Workup

  1. customThe reaction was sealed
  2. temperatureheated to 80 deg. C
  3. filtrationfiltered through celite
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto give a brown oil, which
  6. customwas further purified by silica gel chromatography

Sources & evidence

ORD record
ord-5769bf9f52374d97b847c0e20373826e
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

Loading…