HCID 68970431, compound → HCID 68971441, compound

HRID 1726117Notes

Reaction equation

HRID 1726117 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([OH:25])[C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14](=[O:25])[C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:17][CH:16]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 68970431HCID 68970431, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 68971441HCID 68971441, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[hydroxy-(4-trifluoromethylphenyl)-methyl]-piperidine-1-carboxylic acid tert-butyl ester (1.07 g, 2.98 mmol) in CH2Cl2 (15 mL) were added PCC (1.93 g, 8.94 mmol) and SiO2 (3.86 g) and the mixture was stirred at room temperature for 75 minutes. The mixture was filtered through a silica gel plug (1:4, EtOAc/Hexanes) to afford 4-(4-trifluoromethyl-benzoyl)-piperidine-1-carboxylic acid tert-butyl ester (800 mg, 75%) as a white solid. 1H NMR (CDCl3) δ 1.47 (s, 9H), 1.68-1.75 (m, 2H), 1.85 (d, 2H, J=12.0 Hz), 2.91 (t, 2H, J=11.4 Hz), 3.36-3.43 (m, 1H), 4.13-4.19 (m, 2H), 7.75 (d, 2H, J=8.1 Hz), 8.03 (d, 2H, J=8.1 Hz).

Workup

  1. filtrationThe mixture was filtered through a silica gel plug (1:4, EtOAc/Hexanes)

Sources & evidence

ORD record
ord-d21bed3c940841a8afdf8a41cff4b6c1
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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