Sodium Iodide → HCID 86601997, compound

HRID 1435888Notes

Reaction equation

HRID 1435888 reaction equation
[Na+].[I-].C[Si](Cl)(C)C.O[C:9]1([CH2:23][C:24]([O:26][CH3:27])=[O:25])[C:16]2[N:12]([C:13]3[CH:20]=[CH:19][N:18]=[C:17]([S:21][CH3:22])[C:14]=3[CH:15]=2)[CH2:11][CH2:10]1>CC#N>[CH3:22][S:21][C:17]1[C:14]2[CH:15]=[C:16]3[N:12]([C:13]=2[CH:20]=[CH:19][N:18]=1)[CH2:11][CH2:10][CH:9]3[CH2:23][C:24]([O:26][CH3:27])=[O:25]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 86601996HCID 86601996, compound

Product 1

HCID 86601997HCID 86601997, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To NaI (0.300 g) in CH3CN (3.2 mL) was added TMSCl (0.266 mL). This mixture was added to a suspension of methyl [8-hydroxy-1-(methylthio)-7,8-dihydro-6H-pyrido[3,4-b]pyrrolizin-8-yl]acetate (0.15 g, 0.515 mmol) in CH3CN (1.5 mL), in a water bath. After a period of 0.5 h, the reaction mixture was partitioned between EtOAc and NaHCO3. The organic phase was separated, washed with sodium thiosulphate, dried over MgSO4 and evaporated. The title compound was purified by flash chromatography.

Workup

  1. customthe reaction mixture was partitioned between EtOAc and NaHCO3
  2. customThe organic phase was separated
  3. washwashed with sodium thiosulphate
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe title compound was purified by flash chromatography

Sources & evidence

ORD record
ord-5c4a919abd054ea0abb1f5acc428f99c
Source dataset
uspto-grants-2009_11
Patent number
US07618979B2

Reaction notes

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