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21st June 2012 @ 02:36
Mnr: 31-40

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