Acetone → HCID 18461546, compound

HRID 2303456Notes

Reaction equation

HRID 2303456 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH:12]1[C:16](=[O:17])[O:15][CH:14]2CC=C[CH:13]12.C[N+]1([O-])CC[O:25]CC1.[CH3:29][C:30]([CH3:32])=[O:31]>C(O)(C)(C)C.[Os](=O)(=O)(=O)=O>[OH:31][CH:30]1[CH:32]2[CH:14]([O:15][C:16](=[O:17])[CH:12]2[CH2:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)[CH2:13][CH:29]1[OH:25]

Participants

6

Reactant 3

HCID 180AcetoneHCID 82029Methyl morpholine oxideHCID 9838161HCID 9838161, compound

Product 1

HCID 18461546HCID 18461546, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 6386tert-ButanolSolvent

Procedure

200 mg (0.75 mmol) of the compound from Example 7, 0.08 ml of a 2.5% strength osmium tetroxide solution in tert-butanol and 180 mg of N-methylmorpholine N-oxide were dissolved in 2.5 ml of acetone and stirred at RT for 15 h. The mixture was concentrated and the residue was chromatographed over silica gel (mobile phase: dichloromethane/methanol (100:4)). Yield: 161 mg of a diastereomer mixture. Diastereomer ratio: 1:5:5:1 (HPLC). MS (DCI/NH3): m/e=316 (M+NH4)

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was chromatographed over silica gel (mobile phase: dichloromethane/methanol (100:4))

Sources & evidence

ORD record
ord-3db8c66c193a4a63ba695d42cb8a826d
Source dataset
uspto-grants-2002_08
Patent number
US06433004B1

Reaction notes

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