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3rd May 2015 @ 03:22

Started 6pm Saturday 3rd May - delay uploading due to poor internet connection within School of Chemistry.

Synthesised as part of 'Top 10 Compounds' drive to provide Targets 2 and 3 and derivatives (scale up). 

GitHub Issue: #x


To a stirred solution of LiAlH4 (731 mg, 19.3 mmol, 0.64 equiv.) in anhydrous diethyl ether (20 mL) at 0 ˚C and under Argon was added a solution of crude AEW 219 (~ 30.1 mmol, 1.0 equiv.) in anhydrous diethyl ether (12 mL) over 5 min. The reaction mixture was sirred at 0 ˚C for 1 hour and then at room temp. for 1 hour before reflux for 20 h.

The reaction mixture was cooled to room temp. then to 0 ˚C and saturated ammonium chloride solution (10 mL) was added dropwise followed by dropwise addition of a 10% aqueous solution of NaOH (10 mL) and water (10 mL). The mixture was stirred for ten minutes at 0 ˚C, ten minutes whilst reaching room temp. and then refluxed for ~4 hours before leaving to stir at room temp. overnight.

The white/yellow solid was filtered through CeliteTM and then washed with diethyl ether (5 x 30 mL). Combined organic layers were dried (MgSO4), filtered and evaporated to give a yellow oil that was dried at the high vac.

Purified using Biotage Isolera (hand packed 50g column, 10-100% EtOAc in petroleum ether). Two fractions collected. 



AEW 221-2

Biotage Isolera Data:

aew 221-2 _frac.pdf

Reference NMR from AEW 221-1 below:

Crude NMR 200 MHz

AEW 221-1 crude.pdf
AEW 221-1

200 MHz NMR: Product

Frac One:

AEW 221-1 frac one.pdf
AEW 221-1 frac

Frac Two:

AEW 221-1 frac 2.pdf
AEW 221-1 frac








Hazard and Risk Assessment:

AEW 221-1 HIRAC.pdf


New Symmetrical Chiral Dibenzyl- and Diphenyl-Substituted Diamido-,Dithionoamido-, Diaza-, and Azapyridino-18-crown-6 Ligands
Peter Huszthy, Masatoshi Oue, Jerald S. Bradshaw, Cheng Y. Zhu, Ting

J. Org. Chem., Vol. 57, No. 20, 1992 5383-5394

Linked Entries
Attached Files
AEW 221-2.cdxml
AEW 221-2.png
aew 221-2 _frac.pdf