Exp0302.JPG

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

PiperonalInChI=1/C8H6O3/c9-4-6-1-2-7-8(3-6)11-5-10-7/h1-4H,5H2
2-morpholin ethyl isocyanideInChI=1/C7H12N2O/c1-8-2-3-9-4-6-10-7-5-9/h2-7H2
Boc-Gly-OHInChI=1/C7H13NO4/c1-7(2,3)12-6(11)8-4-5(9)10/h4H2,1-3H3,(H,8,11)(H,9,10)
tert -butylamineInChI=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)