Download our new 2011 product
catalog online: |
 PDF file |  Excel file | SDF file |
|
|
| Typical applications of Bredereck's reagent（CAS:5815-08-7）（18） |
| 2022-06-21 |
|
|
Typical applications of Bredereck's reagent（CAS:5815-08-7）（17）
tert-Butoxybis(dimethylamino)methane
Step 1
A mixture of 1-(tert-butoxycarbonyl)-2-pyrrolidinone (2.96 g, 16 mmol)
with Bredereck’sreagent (2.92 g, 16.8 mmol)(CAS:5815-08-7) in 20 ml of toluene was refluxed for 3 h and then volatiles were removed under reduced pressure.
The residue was triturated with 10 ml of n-hexane,
the solidwas filtered and washed with n-hexane (2 x 5 ml). Yield 3.25 g, 85%
Step 2
To a stirred solution of sodium azide (0.39 g, 6 mmol) and potassium carbonate (1.10 g, 8 mmol)in water (10 mL) was added 3-(chlorosulfonyl)benzoic acid (1.17 g, 5.32 mmol)
and the mixturewas stirred at ambient temperature for 10 min to give a clear solution.
Then tert-butyl (E)-3-((dimethylamino)methylene)-2-oxopyrrolidine-1-carboxylate (0.96 g, 4 mmol) in 10 ml ofacetonitrile was added to the solution and the mixture was stirred for 1 h.
The target diazo lactamwas extracted with chloroform (2 × 15 mL),
the combined organic phases were dried overcalcium chloride and evaporated to dryness.
The residue was purified by columnchromatography on neutral Al2O3 using ethyl acetate-n-hexane 1:3 as eluent. Yield 670 mg, 79%.
[European Journal of Organic Chemistry, 2020, vol. 2020, # 20, p. 3013 - 3018]
|
|
