Triacetoxyperiodinane → HCID 57659527, compound

HRID 217190Notes

Reaction equation

HRID 217190 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH2:15][C:16]2[N:20]=[C:19]([C:21]3[O:29][C:28]4[CH:27]=[CH:26][N:25]=[C:24]([CH2:30][OH:31])[C:23]=4[CH:22]=3)[O:18][N:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH2:15][C:16]2[N:20]=[C:19]([C:21]3[O:29][C:28]4[CH:27]=[CH:26][N:25]=[C:24]([CH:30]=[O:31])[C:23]=4[CH:22]=3)[O:18][N:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 57659420HCID 57659420, compound

Product 1

HCID 57659527HCID 57659527, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[5-(4-hydroxymethylfuro[3,2-c]pyridine-2-yl)-[1,2,4]oxadiazole-3-ylmethoxy]piperidine-1-carboxylic acid tert-butyl ester (Example 24, 25 mg, 58 μmol) in CH2Cl2 was added Dess-Martin periodinane (32 mg, 75 μmol). After 3 h at 20° C., the mixture was diluted with MeOH, adsorbed onto SiO2 and purified by column chromatography to furnish the title compound: RT=3.27 min; m/z (ES+)=429.1 [M+H]+.

Workup

  1. custompurified by column chromatography

Sources & evidence

ORD record
ord-e852c3f73e2041919d9c5dbbadd97bd2
Source dataset
uspto-grants-2012_06
Patent number
US08193359B2

Reaction notes

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