Chlorotrimethylsilane → HCID 178452187, compound

HRID 884341Notes

Reaction equation

HRID 884341 reaction equation
[Zn:1].C[Si](Cl)(C)C.BrCCBr.[C:11]([O:15][C:16]([N:18]1[CH2:21][CH:20]([I:22])[CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]>CC(N(C)C)=O>[I-:22].[C:11]([O:15][C:16]([N:18]1[CH2:21][CH:20]([Zn+:1])[CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 78391,2-DibromoethaneHCID 23994ZincHCID 11000522Tert-butyl 3-iodoazetidine-1-carboxylate

Product 1

HCID 178452187HCID 178452187, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Conditions

Temperature
65 °C

Procedure

Zn dust (1.80 g, 27.5 mmol) was vigorously stirred in DMA (11 ml) under nitrogen and the suspension was heated at 65° C. Trimethylsilyl chloride (0.37 g, 3.39 mmol) and 1,2-dibromoethane (0.64 g, 3.39 mmol) was added and stirring continued for 40 min. A solution of 3-iodo-azetidine-1-carboxylic acid tert-butyl ester (6.00 g, 21.2 mmol) in dimethylacetamide (DMA, 10 ml) was then added dropwise to the solution over a period of 30 min and then the reaction mixture allowed to cool to room temperature over 16 h. The resulting solution was used without any purification in the next step.

Workup

  1. temperatureto cool to room temperature over 16 h
  2. customThe resulting solution was used without any purification in the next step

Sources & evidence

ORD record
ord-6dd1cd814a2a4d8bb3e005b5d492320c
Source dataset
uspto-grants-2012_08
Patent number
US08242102B2

Reaction notes

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