Triacetoxyperiodinane → HCID 90411371, compound

HRID 1521946Notes

Reaction equation

HRID 1521946 reaction equation
[OH:1][CH2:2][CH:3]1[O:8][CH2:7][C:6]([CH3:10])([CH3:9])[N:5]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:4]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)(O)[O-].[Na+]>ClCCl>[CH:2]([CH:3]1[O:8][CH2:7][C:6]([CH3:10])([CH3:9])[N:5]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:4]1)=[O:1]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 90413578HCID 90413578, compound

Product 1

HCID 90411371HCID 90411371, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To as solution of tert-butyl 2-(hydroxymethyl)-5,5-dimethylmorpholine-4-carboxylate (2.0 g, 8.15 mmol) in dichloromethane (25 mL) was added Dess-Martin periodinane (4.15 g, 9.78 mmol) slowly over 10 minutes and the mixture was stirred at room temperature 3 hours. Saturated sodium bicarbonate solution was added and the mixture extracted with dichloromethane. The dichloromethane layer was washed with water and brine, dried over sodium sulfate, filtered, and concentrated to afford the title compound. LCMS: 144.0 (M+H-Boc).

Workup

  1. extractionthe mixture extracted with dichloromethane
  2. washThe dichloromethane layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-525b8cf4c76a451391d8c571f5233389
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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