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

HRID 56408노트

반응식

HRID 56408 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-5b6b9d5443544f8d86e6865dc3d72cb1
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434700B2

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