1-Boc-4-[Hydroxy-(4-trifluoromethoxyphenyl)methyl]piperidine → tert-Butyl 4-(4-(trifluoromethoxy)benzoyl)piperidine-1-carboxylate

HRID 1726241Notes

Reaction equation

HRID 1726241 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([OH:26])[C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[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:26])[C:15]2[CH:16]=[CH:17][C:18]([O:21][C:22]([F:23])([F:24])[F:25])=[CH:19][CH:20]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 120527841-Boc-4-[Hydroxy-(4-trifluoromethoxyphenyl)methyl]piperidineHCID 178418287HCID 178418287, compound

Product 1

HCID 68968884tert-Butyl 4-(4-(trifluoromethoxy)benzoyl)piperidine-1-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[hydroxy-(4-trifluoromethoxy-phenyl)-methyl]-piperidine-1-carboxylic acid tert-butyl ester (see EXAMPLE 32) (604 mg, 1.61 mmol) in CH2Cl2 (8 mL) was added SiO2 (2 g) followed by PCC (1.04 g, 4.82 mmol), and the mixture was stirred at room temperature for 3 h to give 4-(4-trifluoromethoxy-benzoyl)-piperidine-1-carboxylic acid tert-butyl ester as colourless crystals (601 mg, 100%) after purification.

Sources & evidence

ORD record
ord-aa4a1224a10c4668b12cbc71c6360b25
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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