Exp030



=Objective= To obtain a simple Ugi adduct in methanol. =Procedure= To a 25 ml round bottom flask was added [|piperonal] (300mg, 2.0 mmol in 2ml methanol), [|tert -butylamine] (210 µl, 2.0 mmol in 2 ml methanol) and [|Boc-Gly-OH] (350 mg, 2.0mmol in 2ml methanol). After stirring for 10 min [|2-morpholin ethyl isocyanide] (210µl, 2.0 mmol in 2 ml methanol )was added. The mixture was stirred for 24.5 hours and then evaporated. =Results= 1.[| HNMR of 30A] 2.[|C13-NMR of 30A] 3.[|TLC of 30A under UV] and [|stained with ninhydrin](t-butyl amine is highly volatile, therefore no spot was seen on the plate) =Discussion= The H NMR of 30A clearly shows that most of the piperonal is still unreacted. This may be due to the known sluggish behavior of aromatic aldehydes in Ugi reactions, which have been accelerated with Lewis acid catalysts ([|2004 Godet])

=Conclusion= The reaction is incomplete after stirring overnight. Aborted.

=Log=

2006-10-04
1. 14:12] Made-up 2ml of 1M solution of each of the reactants in small vials. 2. 14:20] Added tert-butyl amine (1M 2ml ) to piperonal (1M 2ml), Boc-Gly (1M 2ml) waited for 10 min and then added 2-morpholin ethyl isocyanide (1M 2ml) 3. The reaction is stirred overnight.

2006-10-05
4. 14:45] Methanol from the reaction mixture was evaporated under a gentle flow of Nitrogen gas, the product was dried under high vacuum, a yellow solid **30A** (950mg) was obtained. = = =Tags= [|Piperonal][|InChI=1/C8H6O3/c9-4-6-1-2-7-8(3-6)11-5-10-7/h1-4H,5H2] [|2-morpholin ethyl isocyanide][|InChI=1/C7H12N2O/c1-8-2-3-9-4-6-10-7-5-9/h2-7H2] [|Boc-Gly-OH][|InChI=1/C7H13NO4/c1-7(2,3)12-6(11)8-4-5(9)10/h4H2,1-3H3,(H,8,11)(H,9,10)] [|tert -butylamine][|InChI=1/C4H11N/c1-4(2,3)5/h5H2,1-3H3] ugi030: [|InChI=1/C26H40N4O7/c1-25(2,3)30(21(31)16-28-24(33)37-26(4,5)6)22(18-7-8-19-20(15-18)36-17-35-19)23(32)27-9-10-29-11-13-34-14-12-29/h7-8,15,22H,9-14,16-17H2,1-6H3,(H,27,32)(H,28,33)]

media type="custom" key="6655"