Chlorotrimethylsilane → HCID 178452187, compound

HRID 1849448Notes

Reaction equation

HRID 1849448 reaction equation
[Zn:1].Cl[Si](C)(C)C.BrCCBr.[I:11][CH:12]1[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13]1>CN(C)C(=O)C>[I-:11].[C:19]([O:18][C:16]([N:14]1[CH2:15][CH:12]([Zn+:1])[CH2:13]1)=[O:17])([CH3:22])([CH3:21])[CH3:20]

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×

Procedure

Zinc (2.472 g, 0.03780 mol) was stirred in 10 mL of degassed N,N-dimethylacetamide under N2 atmosphere. Chlorotrimethylsilane (0.411 mL, 0.00324 mol) and 1,2-Dibromoethane (0.233 mL, 0.00270 mol) were added and the mixture was stirred for 20 minutes. Tert-butyl 3-iodoazetidine-1-carboxylate (7.644 g, 0.02700 mol) in degassed N,N-dimethylacetamide (60.0 mL) was added slowly and the cloudy reaction was stirred at room temperature for 1.5 hours to give (1-(tert-butoxycarbonyl)azetidin-3-yl)zinc(II) iodide.

Workup

  1. customthe cloudy reaction
  2. stirringwas stirred at room temperature for 1.5 hours

Sources & evidence

ORD record
ord-2d8dd250bdf04010a4e1d6c8f8f76539
Source dataset
uspto-grants-2015_02
Patent number
US08952043B2

Reaction notes

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