Trimethylsilyl iodide → HCID 57988323, compound

HRID 1666536Notes

Reaction equation

HRID 1666536 reaction equation
[C:1]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:6]=[CH:5][C:4]([C@@:7]2([S:26]([CH2:29][CH2:30][CH3:31])(=[O:28])=[O:27])[CH2:11][N:10](C(OCC3C=CC=CC=3)=O)[C@H:9]([C:22]([O:24][CH3:25])=[O:23])[CH2:8]2)=[CH:3][CH:2]=1.I[Si](C)(C)C>C(#N)C>[C:1]1([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:2]=[CH:3][C:4]([C@@:7]2([S:26]([CH2:29][CH2:30][CH3:31])(=[O:28])=[O:27])[CH2:11][NH:10][C@H:9]([C:22]([O:24][CH3:25])=[O:23])[CH2:8]2)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 57988339HCID 57988339, compound

Product 1

HCID 57988323HCID 57988323, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (2S,4R)-1-benzyl 2-methyl 4-(biphenyl-4-yl)-4-(propylsulfonyl)pyrrolidine-1,2-dicarboxylate (1.85 g, 3.55 mmol) in acetonitrile (30 mL) was added iodotrimethylsilane (1.211 mL, 8.51 mmol) at 0° C. The formed light brown solution was stirred at room temperature for 2 h. Cooled with ice bath, quenched with methanol. Removed the volatiles in vacuo. The residual brown oil was triturated with 2M HCl in ether (20 mL). The formed brown solid was filtered. Washed the cake with ether thoroughly. The collected light brown solid was pumped to afford the desired product (2S,4R)-methyl 4-(biphenyl-4-yl)-4-(propylsulfonyl)pyrrolidine-2-carboxylate (1.54 g, 3.19 mmol, 90% yield). 1H NMR (500 MHz, MeOD) δ ppm 0.97 (t, J=7.32 Hz, 3 H) 1.57-1.71 (m, 2 H) 2.96 (dd, J=9.16, 5.49 Hz, 1 H) 3.22-3.39 (m, 2 H) 3.65 (dd, J=15.72, 4.73 Hz, 1 H) 3.94 (s, 1 H) 4.14 (d, J=13.12 Hz, 1 H) 4.70 (d, J=13.12 Hz, 1 H) 7.37-7.44 (m, 1 H) 7.45-7.54 (m, 2 H) 7.66 (dd, J=19.99, 7.78 Hz, 4 H) 7.79 (d, J=8.55 Hz, 2 H). LC-MS (retention time: 1.42 min, method A), MS m/z 388 (M+H).

Workup

  1. temperatureCooled with ice bath
  2. customquenched with methanol
  3. customRemoved the volatiles in vacuo
  4. customThe residual brown oil was triturated with 2M HCl in ether (20 mL)
  5. filtrationThe formed brown solid was filtered
  6. washWashed the cake with ether thoroughly

Sources & evidence

ORD record
ord-b9121449b0344b45bafcaaf56c7d3a29
Source dataset
uspto-grants-2011_10
Patent number
US08044023B2

Reaction notes

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