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12th February 2013 @ 05:06
Mnr: MNR91-100

Starting material AEW2-2

Attempted 1-pot synthesis of MNR98-1 in an aportic solvent.

 

 

 Hazard Assessment

HIRAC MNR98.pdf

Procedure

To a solution of AEW2-2 (0.10 g, 0.46 mmol) in THF (8 mL) at room temperature was added sodium borohydride (19 mg, 0.51 mmol) follwed by methyl bromoacetate (0.07 mL, 0.76 mmol) and the reaction was left to stir overnight (16 hours).  TLC in the morning showed mainly starting material and a new lower running spot, this looked promising but the spot on the slowly stained blue on sitting, characteristically similar to alcohol MNR97-1.  Actone (5 mL) was added the the mixture was left to stir for 5 mniutes then concentrated under vacuum.  Water (5 mL) was then added and extracted with DCM (10 mL x 3).  The organics were combined, dried, filtered and concentated to give a brown solid.  Crude NMR showed only starting material and degraded alcohol.  Reaction not taken any further forward. 

Strings

Starting material

 InChI=1S/C13H12FNO/c1-9-7-11(8-16)10(2)15(9)13-5-3-12(14)4-6-13/h3-8H,1-2H3

Product

InChI=1S/C16H18FNO3/c1-11-8-13(9-21-10-16(19)20-3)12(2)18(11)15-6-4-14(17)5-7-15/h4-8H,9-10H2,1-3H3

 

NMR

*Feb 2015 - Crude NMR was not uploaded at the time and can't be found on the servers. It may have been mislabelled or it may have been run under another user name seeing as it was just a quick crude run.  

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Attached Files
MNR98-1_table.PNG
MNR98_scheme.png