Acetone → HCID 11537730, compound

HRID 557909Notes

Reaction equation

HRID 557909 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([N:13]3[CH2:17]C=C(C4C=CC=CC=4)C3)=[O:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:24][C:25]([CH3:27])=O.[OH2:28].[C:29]([OH:33])([CH3:32])([CH3:31])[CH3:30].C[N+]1([O-])CCO[CH2:37][CH2:36]1>[Os](=O)(=O)(=O)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:11]([N:13]3[CH2:17][CH:31]([OH:28])[C:29]([C:32]4[CH:37]=[CH:36][CH:27]=[CH:25][CH:24]=4)([OH:33])[CH2:30]3)=[O:12])[CH2:9][CH2:10]2)=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 180AcetoneHCID 962WaterHCID 6386tert-ButanolHCID 82029Methyl morpholine oxideHCID 66662142HCID 66662142, compound

Product 1

HCID 11537730HCID 11537730, compound

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Conditions

Temperature
70 °C

Procedure

To a solution of 1-{[1-(4-chlorophenyl)cyclopropyl]carbonyl}-3-phenyl-2,5-dihydro-1H-pyrrole (80 mg, 0.0002 mol, prepared using a procedure analogous to that described in example 1) in acetone (500 μL, 0.007 mol), water (1250 μL, 0.0694 mol), and tert-butyl alcohol (250 μL, 0.0026 mol), was added osmium tetraoxide (80 mg, 0.00001 mol) followed by 4-methylmorpholine 4-oxide (29 mg, 0.00025 mol). The mixture was heated at 70° C. for 1 hour. After cooling, it was filtered and the filtrate was purified with prep-HPLC to afford the product (36.5 mg). LCMS: m/z 358.0 (M+H)+; 379.9 (M+Na+).

Workup

  1. temperatureAfter cooling
  2. filtrationit was filtered
  3. customthe filtrate was purified with prep-HPLC

Sources & evidence

ORD record
ord-a6e3094b8b7f444286f27832d0be48ad
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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