Cornforth reagent → HCID 57696852, compound

HRID 217627Notes

Reaction equation

HRID 217627 reaction equation
[OH:1][C:2]([CH3:22])([CH3:21])[CH2:3][C@@H:4]1[CH2:8][O:7][C@@:6]([C@@H:10]2[C@:18]3([CH3:19])[C@H:13]([C@@H:14]([OH:20])[CH2:15][CH2:16][CH2:17]3)[CH2:12][CH2:11]2)([CH3:9])[CH2:5]1.C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-][Cr](O[Cr]([O-])(=O)=O)(=O)=O>C(Cl)Cl>[OH:1][C:2]([CH3:22])([CH3:21])[CH2:3][C@@H:4]1[CH2:8][O:7][C@@:6]([C@@H:10]2[C@:18]3([CH3:19])[C@H:13]([C:14](=[O:20])[CH2:15][CH2:16][CH2:17]3)[CH2:12][CH2:11]2)([CH3:9])[CH2:5]1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 86630343HCID 86630343, compound

Product 1

HCID 57696852HCID 57696852, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 13a (123 mg, 0.4 mmol) in dry CH2Cl2 (10 mL) was treated with PDC (pyridinium dichromate, 0.6 g, 1.6 mmol). The mixture was stirred at room temperature for 20 h. The mixture was filtered and concentrated in vacuum. The residue was purified by flash chromatography (SiO2, 3×5.5 cm, 20% EtOAc-hexanes) to give 1S (120 mg, 98%, white solid, mp: 87° C.). Elemental analysis C=73.80%, H=10.51%.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuum
  3. customThe residue was purified by flash chromatography (SiO2, 3×5.5 cm, 20% EtOAc-hexanes)

Sources & evidence

ORD record
ord-185b295b9e53423f834e0074fc9fa58d
Source dataset
uspto-grants-2012_06
Patent number
US08198263B2

Reaction notes

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