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

HRID 872156노트

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HRID 872156 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ccb13fbf62f442aa868e5e7ed3b6e895
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08975260B2

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