Acetone → HCID 53735847, compound

HRID 987091Notes

Reaction equation

HRID 987091 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH:7](CC=C)[N:6]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])=[O:4].C[N+]1([O-])CC[O:28]CC1.S(OS([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].[CH3:43][C:44]([CH3:46])=[O:45]>O.CC(O)(C)C.O=[Os](=O)(=O)=O>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH:7]([CH2:43][CH:44]([OH:45])[CH2:46][OH:28])[N:6]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])=[O:4]

Participants

8

Reactant 4

HCID 180AcetoneHCID 82029Methyl morpholine oxideHCID 9794487Disulfuric acid, sodium salt (1:2)HCID 53856743HCID 53856743, compound2×

Product 1

HCID 53735847HCID 53735847, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×HCID 6386tert-ButanolSolvent

Procedure

6-Allyl-piperidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (Compound 234, 0.087 g, 0.2 mmol) was dissolved in acetone (2 mL) and water (0.25 mL). N-Methylmorpholine oxide (0.068 g, 0.58 mmol) was added, followed by a 2.5% OsO4 solution in t-BuOH (0.14 mL). The mixture reaction was stirred at room temperature for 14 hours. Sodium pyrosulfate (0.3 g) in water (1 mL) was added with stirring, and the resultant solution was filtered through Celite and washed with ethanol (10 mL). The solvents were removed and the residue was purified by flash column chromatography (100% EtOAc) to afford Compound 235 (0.086 g, 89%, as a mixture of isomers). Rf=0.12 and 0.06 (2:1 EtOAc/hexanes).

Workup

  1. customThe mixture reaction
  2. stirringwith stirring
  3. filtrationthe resultant solution was filtered through Celite
  4. washwashed with ethanol (10 mL)
  5. customThe solvents were removed
  6. customthe residue was purified by flash column chromatography (100% EtOAc)

Sources & evidence

ORD record
ord-fd3df31ae118439ba3d42f4bebc951dd
Source dataset
uspto-grants-2003_10
Patent number
US06630472B1

Reaction notes

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