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

HRID 872157Notes

Reaction equation

HRID 872157 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][N:6]([CH:9]2[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10]2)[N:5]=1)([O-])=O>C(O)C>[NH2:1][C:4]1[CH:8]=[CH:7][N:6]([CH:9]2[CH2:10][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:12]2)[N:5]=1

Participants

3

Reactant 1

HCID 86697937tert-Butyl 3-(3-Nitro-1H-pyrazol-1-yl)azetidine-1-carboxylate

Product 1

HCID 66634616tert-Butyl 3-(3-Amino-1H-pyrazol-1-yl)azetidine-1-carboxylateYield 102.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 500-mL Parr reactor bottle was purged with nitrogen and charged with 10% palladium on carbon (50% wet, 100 mg dry weight) and a solution of 105a (1.91 g, 7.23 mmol) in ethanol (25 mL). The bottle was attached to a Parr hydrogenator, evacuated, charged with hydrogen gas to a pressure of 50 psi and shaken for 4 h. After this time, the hydrogen was evacuated, and nitrogen was charged into the bottle. Celite 521 (5 g) was added, and the mixture was filtered through a pad of Celite 521. The filter cake was washed with ethanol (2×25 mL), and the combined filtrates were concentrated to dryness under reduced pressure to afford a 100% yield of 105b (1.76 g) as a light yellow oil: 1H NMR (500 MHz, CDCl3) δ 7.22 (d, 1H, J=2.5 Hz), 5.61 (d, 1H, J=2.5 Hz), 4.80 (quant, 1H, J=7.0 Hz), 4.25 (d, 4H, J=7.0 Hz), 3.77 (br s, 2H), 1.41 (s, 9H).

Workup

  1. customA 500-mL Parr reactor bottle was purged with nitrogen
  2. additioncharged with 10% palladium on carbon (50% wet, 100 mg dry weight)
  3. customevacuated
  4. additioncharged with hydrogen gas to a pressure of 50 psi
  5. customAfter this time, the hydrogen was evacuated
  6. additionnitrogen was charged into the bottle
  7. additionCelite 521 (5 g) was added
  8. filtrationthe mixture was filtered through a pad of Celite 521
  9. washThe filter cake was washed with ethanol (2×25 mL)
  10. concentrationthe combined filtrates were concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-15c23bd6de674c6192ed4db5adb2af6e
Source dataset
uspto-grants-2015_03
Patent number
US08975260B2

Reaction notes

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