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

HRID 56408Notes

Reaction equation

HRID 56408 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-5b6b9d5443544f8d86e6865dc3d72cb1
Source dataset
uspto-grants-2016_09
Patent number
US09434700B2

Reaction notes

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