Triacetoxyperiodinane → HCID 118162456, compound

HRID 707527Notes

Reaction equation

HRID 707527 reaction equation
[CH3:1][N:2]([CH3:22])[CH:3]1[CH2:8][CH2:7][N:6]([CH:9]2[CH2:12][N:11]([C:13]3[N:18]=[C:17]([CH2:19][OH:20])[CH:16]=[CH:15][C:14]=3[F:21])[CH2:10]2)[CH2:5][CH2:4]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[CH3:1][N:2]([CH3:22])[CH:3]1[CH2:4][CH2:5][N:6]([CH:9]2[CH2:10][N:11]([C:13]3[N:18]=[C:17]([CH:19]=[O:20])[CH:16]=[CH:15][C:14]=3[F:21])[CH2:12]2)[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 118162454HCID 118162454, compound

Product 1

HCID 118162456HCID 118162456, compoundYield 134.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixed solution of (6-(3-(4-(dimethylamino)piperidin-1-yl)azetidin-1-yl)-5-fluoropyridin-2-yl)methanol (240 mg, 0.779 mmol) described in Production Example 25-3 and dichloromethane (6.00 mL) was added Dess-Martin periodinane (400 mg) at 0° C. The resultant mixture was stirred for 1.5 hours. Quenched with an aqueous sodium hydrogen carbonate solution and sodium thiosulfate, and the reaction solution was extracted with chloroform. An organic layer was dried over sodium sulfate and then filtrated, and the solvent was then evaporated under a reduced pressure to give the title compound (320 mg). The product was used in the subsequent reaction without further purification.

Workup

  1. customQuenched with an aqueous sodium hydrogen carbonate solution and sodium thiosulfate
  2. extractionthe reaction solution was extracted with chloroform
  3. dry with materialAn organic layer was dried over sodium sulfate
  4. filtrationfiltrated
  5. customthe solvent was then evaporated under a reduced pressure

Sources & evidence

ORD record
ord-1bc2497c63af4cb09a5dd4a2b17d46af
Source dataset
uspto-grants-2015_11
Patent number
US09174998B2

Reaction notes

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