Triacetoxyperiodinane → HCID 86615379, compound

HRID 1436524Notes

Reaction equation

HRID 1436524 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:13]([CH2:14][OH:15])[CH:12]2[CH:16]([CH2:17][O:18][CH3:19])[CH:9]1[CH2:10][CH2:11]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH:13]([CH:14]=[O:15])[CH:12]2[CH:16]([CH2:17][O:18][CH3:19])[CH:9]1[CH2:10][CH2:11]2)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 69015024HCID 69015024, compound

Product 1

HCID 86615379HCID 86615379, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Chill a solution of 3-hydroxymethyl-7-methoxymethyl-2-azabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (0.780 g, 2.87 mmol) in dichloromethane (20 mL) in an ice bath and add Dess-Martin periodinate (1.46 g, 3.44 mmol). Stir the mixture at room temperature for 2 h and quench with 10% aqueous sodium sulfite. Extract the mixture with dichloromethane (3×20 mL). Wash the organic extracts with saturated aqueous sodium chloride, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 25:75 ethyl acetate:hexanes) to give the title compound (0.780 g, 100%).

Workup

  1. customquench with 10% aqueous sodium sulfite
  2. extractionExtract the mixture with dichloromethane (3×20 mL)
  3. washWash the organic extracts with saturated aqueous sodium chloride
  4. dry with materialdry (magnesium sulfate)
  5. concentrationconcentrate
  6. custompurify
  7. wash(silica gel chromatography, eluting with 25:75 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-78cd709fec1f4cf6b6af9d54a06e612d
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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