3-Oxo-azetidine-1-carboxylic acid tert-butyl ester → tert-Butyl 3-[(2-methylpropane-2-sulfinyl)imino]azetidine-1-carboxylate

HRID 509556ノート

反応式

HRID 509556 の反応式
O=[C:2]1[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1.[CH3:13][C:14]([S:17]([NH2:19])=[O:18])([CH3:16])[CH3:15]>C1COCC1.C(O[Ti](OCC)(OCC)OCC)C>[C:14]([S:17]([N:19]=[C:2]1[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1)=[O:18])([CH3:16])([CH3:15])[CH3:13]

参加物

5

反応物 2

HCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 3382465Tert-Butanesulfinamide

生成物 1

HCID 56776988tert-Butyl 3-[(2-methylpropane-2-sulfinyl)imino]azetidine-1-carboxylate収率 24%

試薬・触媒・溶媒 2

HCID 178477244HCID 178477244、化合物触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

A mixture of tert-butyl 3-oxoazetidine-1-carboxylate (4 g, 23.37 mmol), 2-methylpropane-2-sulfinamide (3.12 g, 25.7 mmol) and tetraethoxytitanium (10.66 g, 46.7 mmol) in THF (40 ml) in a 20 ml sealed tube was stirred at 70° C. overnight. The reaction mixture was cooled to room temperature, quenched with water and filtered through a bed of Celite. The solid material was washed with ethyl acetate. The organic layer was separated, dried over Na2SO4, filtered and concentrated to obtain a crude mixture. The crude product was then purified by column chromatography (20% EtOAc in Hexane) to afford tert-butyl 3-(tert-butylsulfinylimino)azetidine-1-carboxylate Yield: 1.5 g (24%). 1H NMR (400 MHz, CDCl3): δ 5.15-4.94 (m, 1H), 4.75 (m, 1H), 4.68 (s, 2H), 1.45 (s, 9H), 1.27 (s, 9H).

後処理

  1. customsealed tube
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customquenched with water
  4. filtrationfiltered through a bed of Celite
  5. washThe solid material was washed with ethyl acetate
  6. customThe organic layer was separated
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto obtain a crude mixture
  11. customThe crude product was then purified by column chromatography (20% EtOAc in Hexane)

出典と根拠

ORDレコード
ord-6457cae56dca409d9ce5a0a4b87ae24c
出典データセット
uspto-grants-2015_08
特許番号
US09096580B2

反応ノート

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