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17th April 2012 @ 09:06
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Hazard and Risk Assessment:
HIRAC MNR7.pdf


Procedure:
rac-MNR11-13 (2.00 g, ) was dissolved in a mixture of EtOH (10 mL) and 1M HCl (50 mL) and heated to reflux for 14 h. The solution was allowed to cool to room temperature then cooled in an ice bath, basified with NaOH to pH 12-13 and extracted with DCM (4 x 50 mL). The organic fractions were combined, dried over magnesium sulphate, filtered and concentrated under reduced pressure to give a light brown solid.

0.437 g

Very low yield, extracted with EtOAC

0.062 g

total recovered

0.499 g, 35 %

The pH of the aqueous layer was taken to 6 by the addition of conc HCl and extracted with EtOAc
12th April 2012 @ 08:07
Resolution of MNR26-1 with (+)-dibenzoyl-D-tartaric acid (MNR5-1)

*SM recovered from unsuccessful resolutions in MNR27

MNR30-1%20scheme.png



Hazard and Risk Assessment:
As for MNR2-1

MNR26-1 (0.60 g, 2.29 mmol) and MNR5-1 (1.1 g, 2.29 mmol) was dissolved in a mixture of IPA (20 mL) and hexane(5 mL) and heated till the reagents went into solution. After standing at room temperature overnight a dark solid was visible but not crystals. This solid was filtered off and washed with IPA:Hex (50:50) to give a light brown solid (0.547 g). A portion of this solid (50 mg) was mixed with water (2 mL) and taken to pH 12 with the addition of NaOH solution (2M) and extracted with EtOAc (4 ml x 3). The organic fractions were combined, dried over magnesium sulphate, filtered and concentrated under reduced pressure to give a light brown oil (17 mg) Chiral HPLC analysis of this showed no ee.

mnr26-1_110412.pdf

mnr30-2_firstfilter.pdf

*note - there has been problems with the HPLC pump and the pressure is jumping between 200-3000 psi. This is the likely reason for the change in retention times. See the standard below for a better rac trace

Upon standing white crystals had started to form in the original filtrate. This were filtered and washed with IPA:Hex (50:50) to give a white solid (0.063 g). This was mixed with water (2 mL) and taken to pH 12 with the addition of NaOH solution (2M) and extracted with EtOAc (4 ml x 3). The organic fractions were combined, dried over magnesium sulphate, filtered and concentrated under reduced pressure to give a clear oil (17 mg) Chiral HPLC analysis of this showed an ee of 70%.

mnr26-1 15EtOH 05mL_120412.pdf

mnr30-2_filter_xstals.pdf
Attached Files