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15th March 2012 @ 04:53
Mnr: 21-30

Hazard and Risk Assessment:

As for MNR1-1

MNR28-3

To a cooled solution of MNR27-1 (0.1 g, 0.38 mmol) in DCM (2 mL) at 0°C was added triethylamine (0.0.8 mL, 0.57 mmol) and cyclohexanecarbonyl chloride (0.06 mL, 0.42 mmol). The solution was stirred overnight at room temperature.

The solution was quenched with water (2 mL) and stirred for a further 30 min. The layers were separated and the organic layer was washed with saturated sodium carbonate solution (5 mL), 0.5 M HCl (5 mL) and brine (5 mL). Dried over magnesium sulfate, filtered and concentrated under reduced pressure to give the crude as an orange oil (0.176 g)

Column:- 50-100 EtOAc/PetEther

Fracs 17-26 - 0.063 g, 0.169 mmol, 44% yield (fraction 21 spilt, one of the major fractions)

Characterisation

mnr28-3_1H.pdf
mnr28-3_col.zip

As a 50:50 mixture of rotamers. Peaks not fully resolved at 300 K

1H NMR (300 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).

mnr28-3_13C.pdf
mnr28-3_col.zip

13C NMR (75 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.

Chiral HPLC

KAB1-2.pdf

 

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Attached Files
mnr28-3 table.PNG
KAB1-2.pdf
mnr28-3_1H.pdf
mnr28-3_13C.pdf
mnr28-3_col.zip
1b R 13C NMR MNR28-3.jpg
1b R 1H NMR MNR28-3.jpg