Sodium Thiosulfate → HCID 10025508, compound

HRID 1784160Notes

Reaction equation

HRID 1784160 reaction equation
[C:1]1([S:7]([C:10]2C=[CH:15][C@H:14](C)[C@H:13]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[C@@H:12]([CH3:26])[CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[N+]1([O-])[CH2:33][CH2:32][O:31]CC1.[O-:35]S([O-])(=S)=O.[Na+].[Na+]>CC(C)=O.O.C(OCC)(=O)C.O=[Os](=O)(=O)=O>[C:1]1([S:7]([C:10]2[C@@H:32]([OH:31])[C@@H:33]([OH:35])[C@H:14]([CH3:15])[C@H:13]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[C@@H:12]([CH3:26])[CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 3

HCID 24477Sodium ThiosulfateHCID 82029Methyl morpholine oxideHCID 9977855HCID 9977855, compound

Product 1

HCID 10025508HCID 10025508, compoundYield 83%

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of dienyl sulfone 33 (45 mg, 0.11 mmol), OsO4 (2 mg, 0.0078 mmol), 4-methylmorpholine N-oxide (27 mg, 0.23 mmol) in acetone (0.5 mL) and H2O (0.5 mL) as co-solvent was stirred at room temperature for 36 h, then saturated aqueous Na2S2O3 (5 mL) was added, and stirred for 30 min. The reaction mixture was diluted with ethyl acetate (10 mL), separated, and the aqueous layer was extracted with ethyl acetate (3×5 mL). The combined organic layers were dried over Na2SO4 and concentrated. The residue was purified by flash column chromatography (ethyl acetate/hexanes; 1:1) to afford 40 mg (83%) of diol 39 as a colorless solid. mp 117.0-119.0° C.; [α]20D=−72.7 (c=1.09, CH2Cl2); 1H NMR (CDCl3, 300 MHz) δ 7.86-7.90 (m, 2H), 7.52-7.67 (m, 3H), 7.31 (d, J=7.5 Hz, 1H), 4.55 (d, J=2.7 Hz, 1H), 3.79 (dd, J=5.4 Hz, 1.5 Hz, 1H), 3.47 (dd, J=9.9 Hz, 2.4 Hz, 1H), 2.82 (m, 2H), 2.35 (m, 1H), 2.06 (br s, 1H), 1.26 (d J=7.5 Hz, 3H), 1.13 (d, J=6.9 Hz, 3H), 0.88 (s, 9H), 0.10 (s, 3H), 0.08 (s, 3H); 13C NMR (CDCl3, 75 MHz) δ 147.9, 140.1, 138.9, 133.4, 129.2, 127.7, 77.5, 71.8, 69.8, 40.1, 35.9, 25.8, 18.0, 17.4, 16.8, −4.5, −4.8; Analytical. Calculated for C21H34O5SSi: C, 59.12; H, 8.03. Found: C, 59.07; H, 7.89.

Workup

  1. stirringstirred for 30 min
  2. customseparated
  3. extractionthe aqueous layer was extracted with ethyl acetate (3×5 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (ethyl acetate/hexanes; 1:1)

Sources & evidence

ORD record
ord-978d8844d75b40e69912f3415fd0a03e
Source dataset
uspto-grants-2009_03
Patent number
US07501535B2

Reaction notes

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