Lithium iodide → tert-Butyl 3-(iodomethyl)azetidine-1-carboxylate

HRID 2174935Notes

Reaction equation

HRID 2174935 reaction equation
S(O[CH2:12][CH:13]1[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14]1)(C1C=CC(C)=CC=1)(=O)=O.[I-:24].[Li+]>CC(C)=O.C(OCC)(=O)C>[C:20]([O:19][C:17]([N:15]1[CH2:16][CH:13]([CH2:12][I:24])[CH2:14]1)=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 2

HCID 66321Lithium iodideHCID 56777214Tert-butyl 3-(tosyloxymethyl)azetidine-1-carboxylate

Product 1

HCID 53249943tert-Butyl 3-(iodomethyl)azetidine-1-carboxylateYield 94.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
35 °C

Procedure

To a solution of 1.94 g of tert-butyl 3-[(tosyloxy)methyl]azetidin-1-carboxylate in 15.5 ml acetone were added 837 mg of lithium iodide and the reaction mixture was stirred for 16 hours at 35° C. After cooling, it was diluted with 200 ml ethyl acetate and the organic phase washed twice with 30 ml portions of water and once with 20 ml saturated sodium chloride solution. After drying over sodium sulphate and filtration, this was concentrated in vacuo. In this manner, 1.6 g of tert-butyl-3-(iodomethyl)azetidin-1-carboxylate were obtained, which was further reacted without purification.

Workup

  1. temperatureAfter cooling
  2. washthe organic phase washed twice with 30 ml portions of water and once with 20 ml saturated sodium chloride solution
  3. dry with materialAfter drying over sodium sulphate and filtration
  4. concentrationthis was concentrated in vacuo

Sources & evidence

ORD record
ord-2d3315b473c34b7d8b7f49eb97bd8fb5
Source dataset
uspto-grants-2015_06
Patent number
US09062041B2

Reaction notes

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