Réaction #420464

Équation de réaction

(1,3-Dioxan-2-ylethyl)-magnesium bromide

(R,E)-2-methyl-N-((1-(naphthalen-2-yl)cyclohexyl)methylene)propane-2-sulfinamide

Na2SO4

→

title compound

Rendement 83.0%

(R)—N-(3-(1,3-dioxan-2-yl)-1-(1-(naphthalen-2-yl)cyclohexyl)propyl)-2-methylpropane-2-sulfinamide

Rendement 83.0%

Solvants

Et2O

Et2O

Conditions de réaction

Traitement

1. 1
   AutreA flame dried flask under N2
2. 2
   workup.ADDITIONwas added dropwise
3. 3
   Températureto warm to RT overnight
4. 4
   workup.WAITAfter 20 h sat'd aqueous
5. 5
   Filtrationthe suspension was filtered
6. 6
   Séchagedried (Na2SO4)
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated
9. 9
   AutrePurification on the Biotage with a 25M column

Mode opératoire

A flame dried flask under N2 was charged with anhydrous Et2O (3 mL) and (1,3-Dioxan-2-ylethyl)-magnesium bromide (0.5M in THF, 6.78 mL, 3.39 mmol) and cooled to −78° C. (R,E)-2-methyl-N-((1-(naphthalen-2-yl)cyclohexyl)methylene)propane-2-sulfinamide (524 mg, 1.54 mmol) in anhydrous Et2O (3 mL) was added dropwise and the solution was stirred at −78° C. for 1 h, then allowed to warm to RT overnight. After 20 h sat'd aqueous Na2SO4 solution (4 mL) was added and the suspension was filtered, dried (Na2SO4), filtered and concentrated. Purification on the Biotage with a 25M column and an ethyl acetate/hexane (0.1% DEA) gradient (0→100% EtOAc over 3 CV, hold at 100% EtOAc for 5 CV) gave the title compound (581 mg, 83%) as a clear oil. HPLC (JPK method) Rt=2.61 min; 1H NMR (400 MHz, CDCl3) 7.85-7.80 (m, 4H), 7.53 (d, J=8.8 Hz, 1H), 7.48-7.45 (m, 2H), 4.38 (t, J=5.13 Hz, 1H), 4.10-3.99 (m, 2H), 3.77-3.62 (m, 2H), 3.25 (d, J=8.8 Hz, 1H), 3.15-3.10 (m, 1H), 2.88 (d, J=12.1 Hz, 1H), 2.51 (d, J=11.7 Hz, 1H), 2.03-1.90 (m, 2H), 1.64-1.59 (m, 4H), 1.49-1.42 (m, 2H), 1.31-1.23 (m, 4H), 1.12 (s, 9H), 0.87-0.83 (m, 1H); 13C NMR (100 MHz, CDCl3) 138.5, 133.6, 132.0, 128.2, 128.1, 127.5, 126.9, 126.2, 126.0, 102.1, 67.0, 66.7, 57.0, 46.4, 35.0, 34.8, 32.8, 26.2 (d), 25.9, 23.3, 22.6, 22.2; LC-MS 10.4 min, (M+1)+458 @10.6 min.

Source