Chlorotrimethylsilane → HCID 178452187, compound

HRID 1618031Notes

Reaction equation

HRID 1618031 reaction equation
[Zn:1].Cl[Si](C)(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]>CN(C)C(=O)C>[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
55 °C

Procedure

To a suspension of zinc dust (390 mg, 5.5 mmol) in N,N-dimethylacetamide (3 mL) was added a solution of chlorotrimethylsilane (70 μL) and 1,2-dibromoethane (48 μL) in N,N-dimethylacetamide (1.5 mL) at a rate to maintain the temperature in the range of 45-65° C. The resulting slurry was aged for 15 min, then a solution of 3-iodo-azetidine-1-carboxylic acid tert-butyl ester (1.42 g, 5.0 mmol) in N,N-dimethylacetaminde (5.5 mL) was slowly added to the mixture described above at a rate to maintain the temperature below 40° C. The resulting reaction mixture was then aged for 30 min at room temperature, then the supernatant was transferred into a flame-dried flask to afford the title compound as a ca. 0.5 M solution.

Workup

  1. temperatureto maintain the temperature below 40° C
  2. customThe resulting reaction mixture
  3. waitwas then aged for 30 min at room temperature
  4. customthe supernatant was transferred into a flame-dried flask

Sources & evidence

ORD record
ord-868d3b2d15544570a2c2db7c23e9b40f
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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