Published by MatTodd on 12 February 2009 - 10:19am


Submitted by Althea Tsang and Matthew H. Todd, School of Chemistry, University of Sydney, NSW 2006, Australia. Checked by Victor Sun, Lakshmi Raj Baratha, Soo-Jean Park, same address.



Preparation of Boc-THIQ


To 1,2,3,4-tetrahydroisoquinoline (2.00 g, 15.0 mmol) in dichloromethane (10 mL), triethylamine (3.1 mL, 22.6 mmol, 1.5 eq) and 4-dimethylaminopyridine (0.180 g, 1.5 mmol, 0.1 eq) were added. Di-tert-butyl dicarbonate (4.92 g, 22.6 mmol, 1.5 eq) was added and the reaction mixture stirred at rt for 24 h. The reaction mixture was diluted with dichloromethane (50 mL), washed with water (50 mL) and the organic portions extracted, dried (MgSO4) and concentratedin vacuoto give a bright yellow oil, which was purified by flash column chromatography (3:1 ethyl acetate:hexane) to give the product as a bright yellow oil (3.49 g, 99%)


TLC (hexane:ethyl acetate, 5:1) after 3.5 hours indicated only product and baseline spots. TLC after 23 h indicated slight appearance of second spot at Rf = 0.38.




1H NMR (CDCl3): δ 1.49 (9H, s, H9), 2.83 (2H, dd,J5.8, 5.8, H4), 3.64 (2H, dd,J5.8, 5.8, H3), 4.57 (2H, s, H1), 7.05 “ 7.35 (4H, m). IR (CHCl3) νmax/cm-11682, 1419, 1173. m/z (ESI) 132.1 (100%).


Reference: Reductive deprotection of allyl, benzyl and sulfonyl substituted alcohols, amines and amides using a naphthalene-catalyzed lithiation, E. Alonso, D. J. Ramon and M. Yus,Tetrahedron1997,53, 14355-14368.




1) Original procedure used 1 N HCl wash as well as sat. NaHCO3 wash. No column chromatography.
2) Dilute NaHCO3 wash used in above procedure, working equally well.
3) Column in 1:1 hexane:ethyl acetate works equally well.



jcbradley's picture

It looks like you already have your procedure and spectrum on ChemSpider: http://www.chemspider.com/Chemical-Structure.10493826.html

The only problem with using a blog post to record a procedure is that you can't correct errors or add content over time in a way that can be tracked. That's why we still use a wiki to record experiments. But if you have something truly finalized then this is a good option.

MatTodd's picture

Sure, but why can't I do that here? e.g. I could add new NMR data, for a different sample, which is tracked by virtue of it being part of this post, or containing an InChI.

MatTodd's picture

ChemSpiderMan has suggested a simple solution to this. For CS to find web pages with material for it to assimilate, we can tag with "loadtochemspider", and the page will be found by Google Alerts. Therefore any web page with data on chemical compounds can be tagged in this way - making it very easy for the synthetic community to have their data incorporated into ChemSpider.

Above entry is now tagged as a test. I encourage others to do the same.


jcbradley's picture

I'm only trying to relate our experience with trying to use a blog as a lab notebook. What you have posted here is a formalized write up. But if you are recording an experiment as you are doing it in a lab notebook there may be 50 revisions as you record the log over time. If you do chromatography you need to record the TLC's of all your fractions. You might have some fractions that are not completely pure and they have their associated NMRs. You might have comments from people about your interpretation. You might uncover some mistakes over time, etc.

But for a formal final write-up a blog post could work well.

jcbradley's picture

Good idea to mention loadtochemspider tag. Very easy to do.

ChemSpiderman's picture

The loadtochemspider tags are coming into my inbox everyday at present so as people tag their articles we will review and deposit as appropriate.


Antony Williams
Building a Structure Centric Community for Chemists
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