Cyclohexane → HCID 68857440, compound

HRID 2101662Notes

Reaction equation

HRID 2101662 reaction equation
C1([Si:7]([CH3:10])([CH3:9])[CH3:8])C=CCC=C1.C[N+]1([O-])[CH2:17][CH2:16][O:15]CC1.[O-:19]S([O-])=O.[Na+].[Na+].[CH2:25]1CC[CH2:28][CH2:27][CH2:26]1>CC(C)=O.O.O=[Os](=O)(=O)=O.CCOC(C)=O>[CH3:10][Si:7]([C:16]1([OH:15])[CH2:17][CH:28]=[CH:27][CH2:26][CH:25]1[OH:19])([CH3:8])[CH3:9]

Participants

9

Reactant 4

HCID 8078CyclohexaneHCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 12063077HCID 12063077, compound

Product 1

HCID 68857440HCID 68857440, compoundYield 95%

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

The allylsilane of Example 25 (0.74 g, 4.9 mmol, 1 eq.) was added to a stirring solution of NMO.H2O (2 g, 14.8 mmol, 3 eq.) and OsO4 (100 μL, 0.25 mmol, 0.05 eq.) in acetone (200 mL) and water (50 mL). The reaction was strirred at room temperature overnight before Na2SO3 (0.25 g) was added and the acetone removed in vacuo. The aqueous layer was extracted with EtOAc (3×100 mL) and the combined organic layers were washed with brine, dried over MgSO4 and the solvent removed in vacuo. Column chromatography (cyclohexane:EtOAc, 60:40, RF=0.25) furnished the product as a colourless oil (0.87 g, 4.7 mmol, 95% yield); 1H NMR (400 MHz, CDCl3) 5.56 (1H, m, H-3), 5.50 (1H, m, H-4), 3.94 (1H, m, H-7), 3.81 (1H, m, H-6), 2.35 (1H, m, H-5), 1.86 (1H, m, H-5′), 1.86 (1H, m, H-2), 0.07 (9H, s, H-1); 13C NMR (100 MHz, CDCl3) δ 125.19 (C-4), 120.82 (C-3), 70.39 (C-6), 68.30 (C-7), 35.73 (C-2), 30.16 (C-5), −2.42 (C-1); IR (neat, cm−1) 3423 (b, OH) 1640 (b, C═C) MS (ESI-, m/z) 185.25 [M−H+].

Workup

  1. additionwas added
  2. customthe acetone removed in vacuo
  3. extractionThe aqueous layer was extracted with EtOAc (3×100 mL)
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-8eccc49931774c5ba4758498a683f27a
Source dataset
uspto-grants-2009_08
Patent number
US07572928B2

Reaction notes

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