Potassium Carbonate → (2R)-2-methyl-1-[2-(4-nitrophenyl)ethyl]pyrrolidine

HRID 2390401Notes

Reaction equation

HRID 2390401 reaction equation
C([C@@H]([C@H](C(O)=O)O)O)(O)=O.[CH3:11][C@@H:12]1[CH2:16][CH2:15][CH2:14][NH:13]1.Br[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)C>[CH3:11][C@@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[CH2:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 792664-Nitrophenethyl bromideHCID 11858493(R)-2-methylpyrrolidine L-tartrate

Product 1

HCID 23635021(2R)-2-methyl-1-[2-(4-nitrophenyl)ethyl]pyrrolidine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

(2R)-2-Methylpyrrolidine L-tartrate (4.0 g, 17.0 mmol), 1-(2-bromoethyl)-4-nitrobenzene (9.8 g, 43 mmol), and potassium carbonate (12 g, 85 mmol), were combined in DMF (20 mL) in a sealed tube at 50° C. and stirred vigorously for 16 hours. The mixture was allowed to cool to room temperature, diluted with diethyl ether (100 mL), washed with water (2 times, 100 mL and then 50 mL), and extracted with 1M HCl (2 times, 50 mL and 25 mL). The aqueous acidic extractions were combined, washed with diethyl ether (50 mL), cooled to 0° C., adjusted to pH 14 with 50% NaOH solution, and extracted with dichloromethane (3 times, 50 mL). The dichloromethane extractions were combined, dried (MgSO4), filtered, and the filtrate concentrated to provide the title compound. 1H NMR (300 MHz, CDCl3) δ 1.08 (d, J=6 Hz, 3 H), 1.43 (m, 1 H), 1.75 (m, 2 H), 1.93 (m, 1 H), 2.19 (q, J=9 Hz, 1 H), 2.34 (m, 2 H), 2.91 (m, 2 H), 3.03 (m, 1 H), 3.22 (td, J=8, 3 Hz, 1 H), 7.38 (d, J=9 Hz, 2 H), 8.15 (d, J=9 Hz, 2 H); MS (DCI/NH3) m/z 235 (M+H)+.

Workup

  1. washwashed with water (2 times, 100 mL
  2. extraction50 mL), and extracted with 1M HCl (2 times, 50 mL and 25 mL)
  3. extractionThe aqueous acidic extractions
  4. washwashed with diethyl ether (50 mL)
  5. temperaturecooled to 0° C.
  6. extractionextracted with dichloromethane (3 times, 50 mL)
  7. extractionThe dichloromethane extractions
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-29496563b4c7480ca5e27c5b67ea2401
Source dataset
uspto-grants-2012_09
Patent number
US08273767B2

Reaction notes

Loading…