URI
URI Label
Revisions
Add to List
Edit Entry
Export:
XML
- February 2014 (4)
- January 2014 (2)
- May 2013 (1)
- April 2013 (1)
- October 2012 (1)
- August 2012 (1)
- July 2012 (1)
- June 2012 (7)
- May 2012 (8)
- April 2012 (2)
- March 2012 (6)
- February 2012 (10)
- January 2012 (3)
- October 2011 (1)
- September 2011 (7)
- August 2011 (5)
- March 2011 (1)
- February 2011 (1)
- January 2011 (4)
- December 2010 (3)
- November 2010 (5)
- October 2010 (12)
- September 2010 (5)
- Compound Index (1)
- Data (1)
- Experiments (84)
- Notes (1)
- Ongoing Experiments (3)
- SDF data (1)
Show/Hide Keys
Hazard and Risk Assessment: As for MNR1-1
ProcedureTo a cooled solution of MNR30-7(0.10 g g, 0.38 mmol) in DCM (2 mL) at 0°C was added triethylamine (0.06 mL, 0.57 mmol) and cyclohexanecarbonyl chloride (0.06 mL, 0.42 mmol). The solution was stirred for a total of 22 hours at room temperature.
(on at 11am 21/6/12)
In the morning, the reaction was quenched with water (3 mL) and stirred for 30 minutes then the organic layer was separated and washed with sodium carbonate solution (5 mL), 1M HCl (5 ml) and brine (5 mL), dried and filtered to give the crude as an orange oil (0.165 g)
The crude was then purified by FCC (50-100% EtOAc/Hex)
Fracs 35-51 0.053 g as a white solid - original nmr contained EtOAc but after taking the product up in DCM and putting under the high vac the product was recovered as a clean white solid
NMR
1H NMR (500 MHz, CDCl3): d = 6.73 (s, 1H), 6.65 (s, 1H), 5.17-5.005 (m, 1H), 4.91-4.79 (m, 1H), 4.78-4.67 (m, 1H), 4.50 (s, 0.5H), 4.44 (s, 0.5H), 4.17-4.02 (m, 1H), 3.87 (s, 6H), 3.00-2.63 (m, 4H) 2.48 (t, J = 11.1 Hz, 1H), 1.93-1.20 (m, 10H).
13C NMR (125 MHz, CDCl3): d =174.8, 164.3, 148.3, 148.1, 126.9, 124.4, 111.7, 108.1, 56.1, 55.9, 54.8, 49.0, 45.3, 40.7, 39.1, 29.2, 29.0, 28.2, 25.7, 25.6.
Chiral HPLC - 99% ee using the CHIRALCEL OD-H column, 25% EtOH:Hex with 0.1% TEA and a flow rate of 0.5 mL/min
IR