HCID 69031225, compound → HCID 11435769, compound

HRID 1867226Notes

Reaction equation

HRID 1867226 reaction equation
[CH3:1][C@@:2]1([OH:15])[C:6]2([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)[C@@H:5]([CH3:13])[CH2:4][C@@H:3]1[OH:14].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[OH:15][C@:2]1([CH3:1])[C:6]2([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)[C@@H:5]([CH3:13])[CH2:4][C:3]1=[O:14]

Participants

4

Reactant 2

HCID 69031225HCID 69031225, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 11435769HCID 11435769, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As described in Example 1, (1R*,2R*,4S*)-/(1R*,2S*,4S*)-1,4-dimethylspiro[4.6]-undecane-1,2-diol (570 mg, 2.69 mmol) was oxidized with pyridinium chlorochromate (630 mg, 2.95 mmol) on Celite® (630 mg) in CH2Cl2 (10+12 mL) at room temp. for 12 h. Standard work-up by vacuum filtration over a pad of Celite® furnished after purification by silica-gel FC (pentane/Et2O, 9:1, Rf=0.10) (1R*,4S*)-1-hydroxy-1,4-dimethylspiro[4.6]undecan-2-one (21 mg, 4%).

Workup

  1. filtrationStandard work-up by vacuum filtration over a pad of Celite®
  2. customfurnished
  3. customafter purification by silica-gel FC (pentane/Et2O, 9:1, Rf=0.10) (1R*,4S*)-1-hydroxy-1,4-dimethylspiro[4.6]undecan-2-one (21 mg, 4%)

Sources & evidence

ORD record
ord-a8e7ae1a7ac3454d972122e2b44051e1
Source dataset
uspto-grants-2009_12
Patent number
US07632791B2

Reaction notes

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