Triacetoxyperiodinane → HCID 86621807, compound

HRID 729474Notes

Reaction equation

HRID 729474 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:29]=[CH:28][CH:27]=[CH:26][C:4]=1[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[N:17]=[CH:16][C:15]([N:18]3[CH:22]=[C:21]([CH2:23][CH2:24][OH:25])[N:20]=[N:19]3)=[CH:14][N:13]=2)[CH2:8][CH2:7]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[F:30][C:2]([F:1])([F:31])[C:3]1[CH:29]=[CH:28][CH:27]=[CH:26][C:4]=1[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[N:17]=[CH:16][C:15]([N:18]3[CH:22]=[C:21]([CH2:23][CH:24]=[O:25])[N:20]=[N:19]3)=[CH:14][N:13]=2)[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 68828516HCID 68828516, compound

Product 1

HCID 86621807HCID 86621807, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 25-mL flask equipped with a magnetic stirbar was added 2-[1-(2-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}pyrimidin-5-yl)-1H-1,2,3-triazol-4-yl]ethanol (50 mg, 0.12 mmol) and dichloromethane (5 mL). To the solution was added Dess-Martin periodinane (59 mg, 0.14 mmol) and the reaction mixture stirred at room temperature for 1 h. The reaction mixture was concentrated and purified by column chromatography through silica gel, eluting with 60:40 Hexanes/EtOAc to 40:60 Hexanes/EtOAc, yielding the desired product as a yellow solid. MS (ESI, Q+) m/z 433 (M+1).

Workup

  1. customInto a 25-mL flask equipped with a magnetic stirbar
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by column chromatography through silica gel
  4. washeluting with 60:40 Hexanes/EtOAc to 40:60 Hexanes/EtOAc

Sources & evidence

ORD record
ord-9d2b463b3729479da67fe8244733bd30
Source dataset
uspto-grants-2009_09
Patent number
US07582633B2

Reaction notes

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