Water → HCID 68857440, compound

HRID 2101663Notes

Reaction equation

HRID 2101663 reaction equation
[CH:1]1([Si:7]([CH3:10])([CH3:9])[CH3:8])[CH:6]=[CH:5][CH2:4][CH:3]=[CH:2]1.C[N+]1([O-])CC[O:15]CC1.[OH2:19].[O-]S([O-])=O.[Na+].[Na+]>C(Cl)Cl.O=[Os](=O)(=O)=O.CCOC(C)=O.C1CCCCC1>[CH3:8][Si:7]([C:1]1([OH:15])[CH2:6][CH:5]=[CH:4][CH2:3][CH:2]1[OH:19])([CH3:10])[CH3:9]

Participants

9

Reactant 4

HCID 962WaterHCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 12063077HCID 12063077, compound

Product 1

HCID 68857440HCID 68857440, compoundYield 54%

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 6344DichloromethaneSolventHCID 8078CyclohexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The allylsilane of Example 25 (0.15 g, 1 mmol, 1 eq.) was added to a stirring solution of NMO.H2O (0.4 g, 3 mmol, 3 eq.) and OsO4 (20 μL, 0.05 mmol, 0.05 eq.) in DCM (50 mL) and the reaction stirred overnight at room temperature. Na2SO3 (0.1 g) was added and the organic layer was washed with H2O (50 mL) and brine (50 mL), 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 (0.1 g, 0.54 mmol, 54% 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. washthe organic layer was washed with H2O (50 mL) and brine (50 mL)
  2. dry with materialdried over MgSO4
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-35cab97a485541838dbcfc2179c87950
Source dataset
uspto-grants-2009_08
Patent number
US07572928B2

Reaction notes

Loading…