2-Methylpyrrolidine → HCID 11748944, compound

HRID 1017779Notes

Reaction equation

HRID 1017779 reaction equation
F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:10]2[CH:11]=[CH:12][CH:13]=C[C:9]=2[N:8]=N1.C(N(CC)C(C)C)(C)C.ON1C2C=CC=CC=2N=N1.[Br:42][C:43]1[C:51]([CH3:52])=[CH:50][C:46]([C:47]([OH:49])=O)=[C:45]([CH2:53][C:54]([O:56][CH2:57][CH3:58])=[O:55])[CH:44]=1.CC1CCCN1>O1CCCC1.O.C(OCC)(=O)C>[Br:42][C:43]1[C:51]([CH3:52])=[CH:50][C:46]([C:47]([N:8]2[CH2:9][CH2:10][CH2:11][CH:12]2[CH3:13])=[O:49])=[C:45]([CH2:53][C:54]([O:56][CH2:57][CH3:58])=[O:55])[CH:44]=1

Participants

8

Reactant 5

HCID 130032-MethylpyrrolidineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 11358513HCID 11358513, compound

Product 1

HCID 11748944HCID 11748944, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

2.2 g (6.85 mmol) of O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate, 2.41 ml (13.9 mmol) of N,N-diisopropylethylamine and 0.27 g (2.0 mmol) of 1-hydroxy-1H-benzotriazole are added successively to a solution of 1.9 g (6.31 mmol) of 4-bromo-2-ethoxycarbonylmethyl-5-methyl-benzoic acid in 660 ml of tetrahydrofuran/H2O (9:1). After 10 minutes' stirring, 0.59 g (6.94 mmol) of rac-2-methyl-pyrrolidine is added, the mixture is stirred for another 19 hours and then diluted with 200 ml of ethyl acetate. The solution obtained is washed with 14% NaCl solution and extracted 2× with ethyl acetate. The combined organic phases are washed with 14% NaCl solution and dried with Na2SO4. After removal of the solvent, by distillation, and flash chromatography (silica gel; methylene chloride/ethanol=98:2) the desired compound is obtained.

Workup

  1. stirringthe mixture is stirred for another 19 hours
  2. customThe solution obtained
  3. washis washed with 14% NaCl solution
  4. extractionextracted 2× with ethyl acetate
  5. washThe combined organic phases are washed with 14% NaCl solution
  6. dry with materialdried with Na2SO4
  7. customAfter removal of the solvent
  8. distillationby distillation, and flash chromatography (silica gel; methylene chloride/ethanol=98:2) the desired compound
  9. customis obtained

Sources & evidence

ORD record
ord-9ba6f7fe0b9f4468a028226db53aa0d0
Source dataset
uspto-grants-2002_11
Patent number
US06479524B1

Reaction notes

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