Triacetoxyperiodinane → HCID 86713198, compound

HRID 1500310Notes

Reaction equation

HRID 1500310 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:19])[CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[N:6][CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(OC(=O)C)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:19])[CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86713197HCID 86713197, compound

Product 1

HCID 86713198HCID 86713198, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl (3-(5-bromopyridin-2-yl)-3-hydroxypropyl)carbamate(224 mg, 0.68 mmol) in ethylacetate (4.5 mL, 0.15 M) had 1.2 equivalents of Dess-Martin periodinane (344 mg, 0.81 mmol) added to it and stirred for 1 hour. The reaction mixture is then filtered and washed with sodium hydrogen carbonate and evaporated to give the title compound (220 mg): MS (ESI+) m/z 273.0 [M−But+H].

Workup

  1. additionadded to it
  2. filtrationThe reaction mixture is then filtered
  3. washwashed with sodium hydrogen carbonate
  4. customevaporated

Sources & evidence

ORD record
ord-229d95fce0d84b2998f750f9e115002c
Source dataset
uspto-grants-2015_12
Patent number
US09206126B2

Reaction notes

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