Triacetoxyperiodinane → HCID 58840790, compound

HRID 1268763Notes

Reaction equation

HRID 1268763 reaction equation
[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][C@@:7]23[CH2:24][C@@H:23]([OH:25])[CH2:22][N:8]2[C:9](=[O:21])[N:10]([C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Cl:20])[CH:14]=2)[C:11]3=[O:12])=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C@@:7]23[CH2:24][C:23](=[O:25])[CH2:22][N:8]2[C:9](=[O:21])[N:10]([C:13]2[CH:14]=[C:15]([Cl:20])[CH:16]=[C:17]([Cl:19])[CH:18]=2)[C:11]3=[O:12])=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 59124109HCID 59124109, compound

Product 1

HCID 58840790HCID 58840790, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (6R,7aS)-7a-(4-bromobenzyl)-2-(3,5-dichlorophenyl)-6-hydroxytetrahydro-1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione (Preparation 4), (0.2 g, 0.42 mmol) in dichloromethane (5 mL) was added Dess-Martin periodane reagent (0.216 g, 0.504 mmol) in one lot at room temperature. The reaction mixture was stirred at room temperature for one hour and partitioned between dichloromethane (15 mL) and 1N NaOH (15 mL). The dichloromethane layer was washed with brine (2×20 mL), dried over sodium sulfate and concentrated to yield the title compound as a foamy solid (0.185 g). Retention time=3.84 min; column: YMC S5 Combiscreen ODS 4.6×50 mm (4 min. gradient); Solvent A=10% MeOH, 90% H2O, 0.2% H3PO4; Solvent B=90% MeOH, 10% H2O and 0.2% H3PO4.

Workup

  1. custompartitioned between dichloromethane (15 mL) and 1N NaOH (15 mL)
  2. washThe dichloromethane layer was washed with brine (2×20 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4f96c98b7aeb4add9f4c390db742a05c
Source dataset
uspto-grants-2007_04
Patent number
US07199125B2

Reaction notes

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