Potassium Carbonate → tert-Butyl 3-(3-Nitro-1H-pyrazol-1-yl)azetidine-1-carboxylate

HRID 872156Notes

Reaction equation

HRID 872156 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][NH:6][N:5]=1)([O-:3])=[O:2].[C:9]([O:13][C:14]([N:16]1[CH2:19][CH:18](I)[CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N+:1]([C:4]1[CH:8]=[CH:7][N:6]([CH:18]2[CH2:17][N:16]([C:14]([O:13][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:15])[CH2:19]2)[N:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11000522Tert-butyl 3-iodoazetidine-1-carboxylateHCID 178526745HCID 178526745, compound

Product 1

HCID 86697937tert-Butyl 3-(3-Nitro-1H-pyrazol-1-yl)azetidine-1-carboxylateYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and nitrogen inlet was charged with DMF (20 mL), 3-nitro-1H-pyrazole (1.00 g, 8.84 mmol), N-tert-butoxycarbonyl-3-iodoazetidine (3.00 g, 10.6 mmol) and potassium carbonate (2.45 g, 17.7 mmol), and the reaction mixture was stirred at 60° C. for 16 h. After this time the reaction was concentrated to dryness under reduced pressure, and the resulting residue was mixed with methylene chloride (15 mL) and water (15 mL). The aqueous layer was separated and extracted with methylene chloride (2×15 mL). The combined organic extracts were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography to afford an 80% yield (1.92 g) of 105a as a yellow oil: 1H NMR (300 MHz, CDCl3) δ 7.64 (d, 1H, J=2.4 Hz), 6.97 (d, 1H, J=2.4 Hz), 5.13 (m, 1H), 4.44 (m, 2H), 4.33 (m, 2H), 1.47 (s, 9H).

Workup

  1. customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and nitrogen inlet
  2. concentrationAfter this time the reaction was concentrated to dryness under reduced pressure
  3. additionthe resulting residue was mixed with methylene chloride (15 mL) and water (15 mL)
  4. customThe aqueous layer was separated
  5. extractionextracted with methylene chloride (2×15 mL)
  6. dry with materialThe combined organic extracts were dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-ccb13fbf62f442aa868e5e7ed3b6e895
Source dataset
uspto-grants-2015_03
Patent number
US08975260B2

Reaction notes

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