2-Azido-2-(6-chlorophenyl-2,3,4,5-d4)-cyclohexanone synthesis
- Product Name:2-Azido-2-(6-chlorophenyl-2,3,4,5-d4)-cyclohexanone
- CAS Number:1336986-09-4
- Molecular formula:C12H8ClD4N3O
- Molecular Weight:253.7208
1336986-08-3
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1336986-09-4
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Yield:1336986-09-4 87%
Reaction Conditions:
with sodium azide in dimethyl sulfoxide at 25; for 5 h;
Steps:
Preparation of 2-azido-2-(2-[2H4]-chlorophenyl-d4)cyclohexanone (9)
NaN3 (0.87 g, 13.37 mmol) was added to a DMSO solution (7 mL) of the 2-bromo-2-(2-[2H4]-chlorophenyl)cyclohexanone 7 (1.30 g, 4.46 mmol) and the mixture was stirred for 5 h at 25 °C. Water (20 mL) was added and the mixture was extracted with ethyl acetate (3 × 20 mL). The combined organic layer was washed with water, brine and then dried over anhydrous MgSO4. The solvent was removed under reduced pressure and crude product obtained was purified by flash chromatography (hexane/EtOAc, 10:1) to afford pure 2-azido-2-(2-[2H4]-chlorophenyl)cyclohexanone 9 (1.10 g, 87%) as colorless oil. 1H NMR (CDCl3, 400 MHz, δ): 1.84-1.88 (m, 2H), 1.94-2.03 (m, 3H), 2.48-2.53 (m, 1H), 2.63-2.67 (m, 2H); 13C NMR (CDCl3, 100.6 MHz, δ): 21.3, 25.5, 37.6, 38.9, 74.1, 127.4 (t), 128.0 (t). 129.7 (t), 131.4 (t), 132.5, 137.1, 203.3; IR (film): 2952, 2098, 1674, 1446, 751 cm-1; MS (EI) m/z: 253.1 (M+, 1), 196.1 (72), 141 (100).
References:
Sulake, Rohidas S.;Chen, Chinpiao;Lin, Huei-Ru;Lua, Ahai-Chang [Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,# 19,p. 5719 - 5721] Location in patent:experimental part
1219795-51-3
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1336986-05-0
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1336986-06-1
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![1-(6-Chlorophenyl-2,3,4,5-d4)-7-oxabicyclo[4.1.0]heptane](/CAS/GIF/1336986-07-2.gif)
1336986-07-2
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