Methanol → HCID 57954436, compound

HRID 221355Notes

Reaction equation

HRID 221355 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH2:15][C:16]2[N:20]=[C:19]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([C:27]#[N:28])[CH:22]=3)[O:18][N:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C[Si](I)(C)C.CO.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[NH:8]1[CH2:13][CH2:12][CH:11]([O:14][CH2:15][C:16]2[N:20]=[C:19]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([C:27]#[N:28])[CH:22]=3)[O:18][N:17]=2)[CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 887MethanolHCID 24477Sodium ThiosulfateHCID 85247Trimethylsilyl iodideHCID 11153354HCID 11153354, compound

Product 1

HCID 57954436HCID 57954436, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 4-[5-(2-cyanopyridin-4-yl)[1,2,4]oxadiazol-3-ylmethoxy]piperidine-1-carboxylic acid tert-butyl ester (Example 42, 2.0 g, 5.2 mmol) in chloroform (100 ml) under argon, was added trimethylsilyl iodide (2.95 ml, 20.8 mmol) and the reaction mixture stirred for 1 h MeOH was added until a solution formed then sodium thiosulphate (6.6 g, 41.5 mmol) was added and the reaction mixture stirred vigorously for 10 min. The solids were removed by filtration and the filtrate adsorbed onto silica gel. Purification via column chromatography (DCM-MeOH, 9:1) afforded the title compound: RT=1.92 min; m/z (ES+)=286.0 [M+H]+.

Workup

  1. additionwas added until a solution
  2. customformed
  3. customThe solids were removed by filtration
  4. customPurification via column chromatography (DCM-MeOH, 9:1)

Sources & evidence

ORD record
ord-d3404be3cc5b402488cf5445e0337dca
Source dataset
uspto-grants-2012_06
Patent number
US08207147B2

Reaction notes

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