3-Oxo-azetidine-1-carboxylic acid tert-butyl ester → 1383372-62-0

HRID 1051157ノート

反応式

HRID 1051157 の反応式
[C:1]([N:8]1[CH2:11][C:10](=[O:12])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:13]([Mg]Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1>[CH2:13]([C:10]1([OH:12])[CH2:11][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

4

反応物 2

HCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 178419663HCID 178419663、化合物

生成物 1

HCID 659192071383372-62-0収率 70%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

1-Boc-3-azetidinone (1) (2.0 gm, 11.68 mmol) was dissolved in dry THF (20 ml) under nitrogen and cooled to 0° C. Then the solution was added 2.0 M solution of Benzyl magnesium bromide (2) in THF (8.76 ml, 17.52 mmol) under nitrogen atmosphere. The reaction mixture was then allowed to warm to room temperature and stirred for 1 h. The reaction completion was monitored by TLC. The reaction was quenched by the addition of saturated ammonium chloride solution and extracted ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. Crude product was then purified by column chromatography to give compound 3 (2.15 gm, 70%). 1H NMR (400 MHz, DMSOd6) δ: 1.40 (s, 9H), 2.25 (s, 2H), 4.00 (d, 2H), 4.35 (d, 2H), 6.05 (s, 1H), 7.18 (m, 3H), 7.25 (d, 2H); MS: m/z 263.90 (M+1)+.

後処理

  1. temperatureto warm to room temperature
  2. customThe reaction was quenched by the addition of saturated ammonium chloride solution
  3. extractionextracted ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customCrude product was then purified by column chromatography

出典と根拠

ORDレコード
ord-322df25e281545b387f3ece0a37662be
出典データセット
uspto-grants-2016_07
特許番号
US09388164B2

反応ノート

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