Trimethylsilyl iodide → 2-((1S,2R,3S,5S)-3-aminobicyclo[3.1.0]hexan-2-yl)isoindoline-1,3-dione

HRID 56408ノート

反応式

HRID 56408 の反応式
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C@H:12]1[C@@H:17]([NH:18]C(=O)OCC2C=CC=CC=2)[CH2:16][C@H:15]2[C@@H:13]1[CH2:14]2.C[Si](I)(C)C>C(Cl)(Cl)Cl>[NH2:18][C@H:17]1[CH2:16][C@H:15]2[C@H:13]([CH2:14]2)[C@H:12]1[N:3]1[C:4](=[O:11])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]1=[O:1]

参加物

4

反応物 2

HCID 85247Trimethylsilyl iodideHCID 118048962benzyl (1S,2R,3S,5S)-2-(1,3-dioxoisoindolin-2-yl)bicyclo[3.1.0]hexan-3-ylcarbamate

生成物 1

HCID 1180362842-((1S,2R,3S,5S)-3-aminobicyclo[3.1.0]hexan-2-yl)isoindoline-1,3-dione

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

To a solution of benzyl (1S,2R,3S,5S)-2-(1,3-dioxoisoindolin-2-yl)bicyclo[3.1.0]hexan-3-ylcarbamate (4.0 g, 10.638 mmol) in chloroform (30 mL) at room temperature was added trimethylsilyl iodide (14.6 mL, 106.380 mmol) dropwise, and the resulting mixture was stirred at room temperature for 1 hour. The reaction was quenched with methanol (5 mL), diluted with ethyl acetate (150 mL), and washed with water (3×50 mL) and brine (50 mL). The organic layer was dried over sodium sulfate, filtered and concentrated to afford a crude compound, which was directly used in the next reaction without further purification. MS (ES+) C14H14N2O2 requires: 242, found: 243 [M+H]+.

後処理

  1. customThe reaction was quenched with methanol (5 mL)
  2. additiondiluted with ethyl acetate (150 mL)
  3. washwashed with water (3×50 mL) and brine (50 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-5b6b9d5443544f8d86e6865dc3d72cb1
出典データセット
uspto-grants-2016_09
特許番号
US09434700B2

反応ノート

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