Potassium Carbonate → (2S,3'S)-2-Methyl-1'-(6-methyl-5-nitro-pyridin-2-yl)-[1,3']bipyrrolidinyl

HRID 2401102Notes

Reaction equation

HRID 2401102 reaction equation
Cl.Cl.[CH3:3][C@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C@H:9]1[CH2:13][CH2:12][NH:11][CH2:10]1.Cl[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[C:17]([CH3:24])[N:16]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:3][C@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C@H:9]1[CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[C:17]([CH3:24])[N:16]=2)[CH2:10]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2531236-Chloro-2-methyl-3-nitropyridineHCID 67422681(2S,3'S)-2-Methyl-[1,3']bipyrrolidinyl dihydrochloride

Product 1

HCID 71280938(2S,3'S)-2-Methyl-1'-(6-methyl-5-nitro-pyridin-2-yl)-[1,3']bipyrrolidinylYield 82.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of (2S,3′S)-2-methyl-[1,3′]bipyrrolidinyl dihydrochloride (0.596 g, 2.64 mmol,) in acetonitrile (25 mL) was added 2-chloro-5-nitro-6-picoline (0.685 g, 3.96 mmol,) and powder potassium carbonate (1.45 g, 10.6 mmol), then heated to 65° C. for 4.0 hr, then at 45° C. for 16 hr. The reaction mixture was then allowed to cool to room temperature and filtered through a 10 g Varian Bond Elut SCX (strong cation-exchange) cartridge eluting with 50 mL of (1:1) methanol in dichloromethane, 25 mL of methanol, followed by 7N ammonia in methanol (50 mL). The filtrate was concentrated under vacuum, to afford 0.633 g (82%) of the title compound.

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered through a 10 g Varian Bond Elut SCX (strong cation-exchange) cartridge
  3. washeluting with 50 mL of (1:1) methanol in dichloromethane, 25 mL of methanol
  4. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-7732649dba0f4e83a00682e8241f069c
Source dataset
uspto-grants-2014_08
Patent number
US08796278B2

Reaction notes

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