Allyl iodide → tert-butyl (S)-2-(allyloxy)-1-((S)-oxiran-2-yl)ethylcarbamate

HRID 20042

Reaction equation

HRID 20042 reaction equation
[OH:1][CH2:2][C@H:3]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[C@H:4]1[CH2:6][O:5]1.[CH2:15](I)[CH:16]=[CH2:17]>C1(C)C=CC=CC=1.[Ag-]=O>[CH2:17]([O:1][CH2:2][C@H:3]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[C@H:4]1[CH2:6][O:5]1)[CH:16]=[CH2:15]

Participants

5

Reactant 2

HCID 11166Allyl iodideHCID 86614133tert-butyl (S)-2-hydroxy-1-((S)-oxiran-2-yl)ethylcarbamate

Product 1

HCID 86614132tert-butyl (S)-2-(allyloxy)-1-((S)-oxiran-2-yl)ethylcarbamate

Reagents, catalysts & solvents 2

HCID 178418778HCID 178418778, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of tert-butyl (S)-2-hydroxy-1-((S)-oxiran-2-yl)ethylcarbamate (0.125 g, 0.6 mmol; see: Kurokawa, N.; Ohfune, Y. Tetrahedron 1993, 49, 6195) in toluene (6 mL), was added allyliodide 0.3 mL, 3 mmol) followed by silver(I) oxide (0.7 g, 3 mmol). The solution was stirred at 65° C. in a darkened hood for a period of 15 h. The mixture was then cooled to ambient temperature, filtered through Celite, washed with CH2Cl2, and conc. in vacuo. Purification on SiO2 (10-20% EtoAc/Hexanes) gave the title compound as a yellow oil.

Workup

  1. temperatureThe mixture was then cooled to ambient temperature
  2. filtrationfiltered through Celite
  3. washwashed with CH2Cl2
  4. customPurification on SiO2 (10-20% EtoAc/Hexanes)

Sources & evidence

ORD record
ord-71e22a70ba924d01bbdb8094577fa4cf
Source dataset
uspto-grants-2010_06
Patent number
US07745484B2

Linked notes

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