Water → HCID 18009504, compound

HRID 987597Notes

Reaction equation

HRID 987597 reaction equation
[C:1]1([C:7]2([CH2:14][NH:15][C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH3:25])=[O:17])[CH2:12][CH2:11][C:10](=[CH2:13])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[OH2:32].[OH:33]S([O-])=O.[Na+]>C1COCC1.O=[Os](=O)(=O)=O>[OH:32][C:10]1([CH2:13][OH:33])[CH2:9][CH2:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([CH2:14][NH:15][C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH3:25])=[O:17])[CH2:12][CH2:11]1

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 18009445HCID 18009445, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 18009504HCID 18009504, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-phenyl-1-(3-(2-methoxyphenyl)-3-oxo-2-azaprop-1-yl)-4-methylidenecyclohexane (Example 165, 22.3 mg, 0.66 mmol) in 1.0 mL of THF was added OsO4 (33.8 mg, 0.13 mmol), pyridine (0.5 mL) and water (0.5 mL). The mixture was stirred at rt for 17 h. To the reaction mixture was then added 1 mL of saturated NaHSO3 solution. After 1 h, the volatiles were removed by vacuum and the residue was loaded onto silica gel and eluted with first EtOAc/Hexane (1:1) then EtOAc to give the title compound as a 2:1 mixture of diastereomers.

Workup

  1. waitAfter 1 h
  2. customthe volatiles were removed by vacuum
  3. washeluted with first EtOAc/Hexane (1:1)

Sources & evidence

ORD record
ord-09ce907893294c8b97c2e1ee5df13f94
Source dataset
uspto-grants-2003_10
Patent number
US06632836B1

Reaction notes

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