Acetone → HCID 54142852, compound

HRID 849144Notes

Reaction equation

HRID 849144 reaction equation
[CH2:1]([O:3][C:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]([CH2:11][CH:12](CC=C)[CH2:13][C:14]([O:16][CH3:17])=[O:15])[N:10]=1)[CH3:2].C[N+]1([O-])CC[O:25]CC1.Cl.[CH3:30][C:31]([CH3:33])=[O:32]>O.[Os](=O)(=O)(=O)=O>[OH:32][CH:31]([CH2:33][OH:25])[CH2:30][CH:12]([CH2:11][CH:9]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[N:10]1)[CH2:13][C:14]([O:16][CH3:17])=[O:15]

Participants

7

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 82029Methyl morpholine oxideHCID 53770180HCID 53770180, compound

Product 1

HCID 54142852HCID 54142852, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

Example 212 A) The title product of Example 211 dissolved in a 1:1 mixture of acetone and water and treated with osmium tetraoxide (2.5 equivalent %) and 4-methylmorpholine oxide (2 equivalents) at room temperature is allowed to stir overnight. The mixture is then carefully neutralized with dilute HCl, concentrated on a rotary evaporator, and extracted with 3 portions of EtOAc. The combined organic extracts are then dried (Na2SO4), stripped and purified by column chromatography on silica gel to yield methyl b-(2,3-dihydroxypropyl)-7-ethoxy-3,4,5,6-tetrahydro-2H-azepine-2-butanoate

Workup

  1. concentrationconcentrated on a rotary evaporator
  2. extractionextracted with 3 portions of EtOAc
  3. dry with materialThe combined organic extracts are then dried (Na2SO4)
  4. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-e3dc37972d1e4b60b8a807ef1c191519
Source dataset
uspto-grants-2000_01
Patent number
US06011028

Reaction notes

Loading…