Sodium Sulfate → HCID 58954840, compound

HRID 333282Notes

Reaction equation

HRID 333282 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[CH2:7][CH2:8][Mg]Br.[CH3:11][C:12]([S@:15](/[N:17]=[CH:18]/[C:19]1([C:25]2[CH:34]=[CH:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)=[O:16])([CH3:14])[CH3:13].[O-]S([O-])(=O)=O.[Na+].[Na+]>CCOCC>[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[CH2:7][CH2:8][CH:18]([NH:17][S@@:15]([C:12]([CH3:14])([CH3:13])[CH3:11])=[O:16])[C:19]1([C:25]2[CH:34]=[CH:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=2)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 178419673HCID 178419673, compoundHCID 178455558HCID 178455558, compound

Product 1

HCID 58954840HCID 58954840, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-78 °C

Procedure

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.

Workup

  1. customA flame dried flask under N2
  2. additionwas added dropwise
  3. temperatureto warm to RT overnight
  4. waitAfter 20 h sat'd aqueous
  5. filtrationthe suspension was filtered
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification on the Biotage with a 25M column

Sources & evidence

ORD record
ord-0da7276280fd436e93209773d67af329
Source dataset
uspto-grants-2014_11
Patent number
US08877975B2

Reaction notes

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