Triethylamine → Tert-butyl methyl(1-(5-nitropyridin-2-yl)pyrrolidin-3-yl)carbamate

HRID 2271538Notes

Reaction equation

HRID 2271538 reaction equation
[CH3:1][N:2]([CH:10]1[CH2:14][CH2:13][NH:12][CH2:11]1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].C(N(CC)CC)C.Cl[C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][N:24]=1>C1COCC1.C([O-])(O)=O.[Na+]>[CH3:1][N:2]([CH:10]1[CH2:14][CH2:13][N:12]([C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][N:24]=2)[CH2:11]1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:6])[CH3:7]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 783082-Chloro-5-nitropyridineHCID 27614043-(N-tert-Butoxycarbonyl-N-methylamino)pyrrolidine

Product 1

HCID 58386085Tert-butyl methyl(1-(5-nitropyridin-2-yl)pyrrolidin-3-yl)carbamateYield 100.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of tert-butyl methyl(pyrrolidin-3-yl)carbamate (1.00 g, 5.0 mmol) in THF (25 mL) was added triethylamine (0.70 mL, 5.0 mmol) and 2-chloro-5-nitropyridine (500 mg, 3.15 mmol). The reaction mixture was then stirred at room temperature for 16 h, diluted with a saturated NaHCO3 solution and extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated. Purification by column chromatography (silica, ethyl acetate/hexanes) afforded the desired product (1.02 g, 100%) as a yellow solid. ESI MS m/z 323 [C15H22N4O4+H]+

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customPurification by column chromatography (silica, ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-6400d712c9104e859f46889016926d8e
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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