Methanol → HCID 11652480, compound

HRID 217173Notes

Reaction equation

HRID 217173 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[N:19]=[C:18]([C:20]3[O:28][C:27]4[CH:26]=[CH:25][N:24]=[C:23]([C:29]#[N:30])[C:22]=4[CH:21]=3)[O:17][N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[Si](I)(C)(C)C.CO.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[NH:8]1[CH2:9][CH2:10][CH:11]([CH2:14][C:15]2[N:19]=[C:18]([C:20]3[O:28][C:27]4[CH:26]=[CH:25][N:24]=[C:23]([C:29]#[N:30])[C:22]=4[CH:21]=3)[O:17][N:16]=2)[CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 887MethanolHCID 24477Sodium ThiosulfateHCID 85247Trimethylsilyl iodideHCID 57659496HCID 57659496, compound

Product 1

HCID 11652480HCID 11652480, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A stirred solution 4-[5-(4-cyanofuro[3,2-c]pyridin-2-yl)-[1,2,4]oxadiazol-3-ylmethyl]-piperidine-1-carboxylic acid tert-butyl ester (Example 82, 134 mg, 328 μmol) in anhydrous CHCl3 (7 mL) was treated with TMS-I (140 μL, 983 μmol). After 1 h, the reaction was treated with MeOH (3.4 mL), then solid Na2S2O3 was added slowly to remove the yellow colour. The reaction mixture was filtered and the excess Na2S2O3 collected was washed with MeOH (3×1 mL). The combined filtrates were allowed to stand for 1 h, before being purified by column chromatography (MeOH—CH2Cl2, 1:9) to yield the title compound: RT=2.44 min; m/z (ES+)=310.1 [M+H]+.

Workup

  1. customto remove the yellow colour
  2. filtrationThe reaction mixture was filtered
  3. customthe excess Na2S2O3 collected
  4. washwas washed with MeOH (3×1 mL)
  5. waitto stand for 1 h
  6. custombefore being purified by column chromatography (MeOH—CH2Cl2, 1:9)

Sources & evidence

ORD record
ord-90a554613277402a92efccfa96bf9600
Source dataset
uspto-grants-2012_06
Patent number
US08193359B2

Reaction notes

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