3-Methyl-3-(pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylic acid tert-butyl ester → (3-Methylpyrrolidin-3-yl)(pyrrolidin-1-yl)methanone

HRID 1945496Notes

Reaction equation

HRID 1945496 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C:10]([CH3:20])([C:13]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[O:14])[CH2:9]1)=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl.O>[CH3:20][C:10]1([C:13]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[O:14])[CH2:11][CH2:12][NH:8][CH2:9]1

Participants

5

Reactant 1

HCID 596056303-Methyl-3-(pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 63140531(3-Methylpyrrolidin-3-yl)(pyrrolidin-1-yl)methanoneYield 79.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 3-methyl-3-(pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylic acid tert-butyl ester (330 mg, 1.17 mmol) in TFA (5 mL), DCM (5 mL) and water (0.1 mL) was stirred at room temperature for 2 hours and then concentrated under reduced pressure. The residue was taken up in MeOH and loaded onto an Isolute® SCX-2 cartridge (10 g). The cartridge was washed with MeOH and the desired product was eluted with 2M NH3 in MeOH. The solvents were removed to give (3-Methylpyrrolidin-3-yl)pyrrolidin-1-ylmethanone as a white solid (169 mg, 79%). 1H NMR (400 MHz, CHCl3-d): δ 3.55-3.40 (m, 5 H); 3.06-2.92 (m, 2 H); 2.32-2.20 (m, 2 H); 2.01-1.82 (m, 5 H); 1.71 (m, 1 H); 1.33 (s, 3 H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. washThe cartridge was washed with MeOH
  3. washthe desired product was eluted with 2M NH3 in MeOH
  4. customThe solvents were removed

Sources & evidence

ORD record
ord-5afd057523c6456fbe594783550aed88
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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