Triacetoxyperiodinane → 4-(2-Thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinecarbaldehyde

HRID 1972421Notes

Reaction equation

HRID 1972421 reaction equation
C([O:8][CH2:9][CH:10]1[CH2:15][N:14]([S:16]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)(=[O:18])=[O:17])[CH2:13][CH2:12][N:11]1[C:24]1[CH:29]=[CH:28][C:27]([C:30]([OH:36])([CH3:35])[C:31]([F:34])([F:33])[F:32])=[CH:26][CH:25]=1)C1C=CC=CC=1.C(=O)(O)[O-].[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[S:20]1[CH:21]=[CH:22][CH:23]=[C:19]1[S:16]([N:14]1[CH2:13][CH2:12][N:11]([C:24]2[CH:25]=[CH:26][C:27]([C:30]([OH:36])([CH3:35])[C:31]([F:33])([F:32])[F:34])=[CH:28][CH:29]=2)[CH:10]([CH:9]=[O:8])[CH2:15]1)(=[O:17])=[O:18]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 665825752-(4-(2-((Benzyloxy)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol

Product 1

HCID 866703254-(2-Thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinecarbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1,1,1-trifluoro-2-(4-(2-(hydroxymethyl)-4-(thiophen-3-ylsulfonyl)piperazin-1-yl)phenyl)-2-propanol hydrochloride (50 mg, 0.103 mmol, Example 44) in CH2Cl2 (2.0 mL) at room temperature was added solid sodium bicarbonate (17.25 mg, 0.205 mmol) followed by Dess-Martin periodinane (47.9 mg, 0.113 mmol, Sigma-Aldrich, St. Louis, Mo.). The reaction was stirred at this temperature for 30 min and then filtered through a pad of Celite® (diatomaceous earth) eluting with CH2Cl2. The filtrate was concentrated to yield 4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinecarbaldehyde which was used without purification.

Workup

  1. filtrationfiltered through a pad of Celite® (diatomaceous earth)
  2. washeluting with CH2Cl2
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-48d48e7e29ad4639b99a4b02e6509814
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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