Ammonium formate → HCID 10464367, compound

HRID 370364Notes

Reaction equation

HRID 370364 reaction equation
C([N:8]1[CH2:12][CH2:11][C@@H:10]([C@@H:13]([NH:15][CH3:16])[CH3:14])[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[OH-].[OH-].[Pd+2].C(Cl)Cl.CO>[CH3:16][NH:15][C@H:13]([C@@H:10]1[CH2:11][CH2:12][NH:8][CH2:9]1)[CH3:14]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 9904942HCID 9904942, compound

Product 1

HCID 10464367HCID 10464367, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

(R,S)-1-benzyl-3-[1'-(methylamino)ethyl]pyrrolidine (0.51 g of crude product) is dissolved in MeOH (10 ml) under a N2 atmosphere, Pearlman's catalyst and ammonium formate (0.89 g, 14.11 mmol) are then added. The reaction mixture is refluxed for 12 hours. The reaction mixture is then diluted with CH2Cl2 :MeOH (1:1) and filtered through a celite pad. The filtrate is washed with 15% aqueous NaOH:brine (1:1) and the aqueous layer is back extracted with CH2Cl2 (2×). The combined organic layers are dried over MgSO4, filtered and concentrated under a stream of N2 to give crude (R,S)-3-[1'-(methylamino)ethyl]pyrrolidine: 1H NMR (300 MHz, CDCl3) δ 1.05 (d, J is 6.3 Hz, 3H), 1.43 (ddd, J is 17, 12, 9 Hz, 1H), 1.87 (m, 1H), 2.02 (dd, J is 16, 8 Hz, 1H), 2.38 (s, 3H), 2.41 (m, 1H), 2.61 (broad s, 2H), 2.65 (dd, J is 11, 8 Hz, 1H), 2.91-3.00 (m, 2H), 3.13 (dd, J is 11, 8 Hz, 1H). This material is suitable for use in various reactions including but not limited to the synthesis of quinolones.

Workup

  1. temperatureThe reaction mixture is refluxed for 12 hours
  2. filtrationfiltered through a celite pad
  3. washThe filtrate is washed with 15% aqueous NaOH:brine (1:1)
  4. extractionthe aqueous layer is back extracted with CH2Cl2 (2×)
  5. dry with materialThe combined organic layers are dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under a stream of N2

Sources & evidence

ORD record
ord-240182b5c2eb42ee87300d5b28f6cf85
Source dataset
uspto-grants-2000_10
Patent number
US06140510

Reaction notes

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