tert-butyl3-(4-nitro-1H-pyrazol-1-yl)azetidine-1-carboxylate synthesis

6synthesis methods

Product Name:tert-butyl3-(4-nitro-1H-pyrazol-1-yl)azetidine-1-carboxylate
CAS Number:1314987-79-5
Molecular formula:C11H16N4O4
Molecular Weight:268.27

2075-46-9 Synthesis

2075-46-9
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141699-58-3 Synthesis

1-(Tert-butoxycarbonyl)-3-(methanesulfonyloxy)azetidine

141699-58-3
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tert-butyl3-(4-nitro-1H-pyrazol-1-yl)azetidine-1-carboxylate

1314987-79-5
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Yield:1314987-79-5 93%

Reaction Conditions:

with caesium carbonate in N,N-dimethyl-formamide at 90; for 12 h;

Steps:

30.1 Step 1: Synthesis of tert-butyl-3-(4-nitro-1H-pyrazol-1-yl)azetidin-1-carboxylate

4-Nitro-1H-pyrazole (2.9 g, 25.77 mmol) was dissolved in DMF (30 ml). Cs₂CO₃ (17.6 g, 2.0 eq.) and tert-butyl-3-(methylsulfonyloxy)azetidin-1-carboxylate (6.8 g, 1.05 eq., Intermediate 21) were added thereto, followed by stirring thereof at 90°C for 12 hours. Water was added thereto to terminate the reaction. It was extracted three times with ethyl acetate, dried over MgSO₄, and concentrated. It was subjected to column chromatography (MeOH:MC = 1:40) to obtain 6.45 g of the target compound in yellow color (yield: 93%). MS (ESI) m/z : 268.9 [M+H]⁺; ¹H NMR (300 MHz, CDCl₃) δ 8.30 (s, 1H), 8.14 (s, 1H), 5.09-5.03 (m, 1H), 4.44-4.29 (m, 4H), 1.46 (s, 9H).

References:

EP3722298,2020,A1 Location in patent:Paragraph 0147

2075-46-9 Synthesis

2075-46-9
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141699-55-0 Synthesis