Sodium Iodide → Tert-butyl[2-oxo-3-(3,4,5-trifluorophenyl)piperidin-1-yl]carbamate

HRID 2235707Notes

Reaction equation

[I-].[Na+].[H-].[Na+].N1(O[CH2:15][CH2:16][CH2:17][CH:18]([C:30]2[CH:35]=[C:34]([F:36])[C:33]([F:37])=[C:32]([F:38])[CH:31]=2)[C:19]([NH:21][NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:20])C2C=CC=CC=2N=N1.O.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[C:26]([O:25][C:23](=[O:24])[NH:22][N:21]1[CH2:15][CH2:16][CH2:17][CH:18]([C:30]2[CH:35]=[C:34]([F:36])[C:33]([F:37])=[C:32]([F:38])[CH:31]=2)[C:19]1=[O:20])([CH3:29])([CH3:28])[CH3:27]

Participants

Conditions

Temperature: 100 °C

Procedure

Sodium iodide (131 mg) and sodium hydride (containing mineral oil at 40%, 70 mg) were added to a solution of tert-butyl N′-[5-(benzotriazol-1-yloxy)-2-(3,4,5-trifluorophenyl)pentanoyl]hydrazinecarboxylate (420 mg) in DMF (3 mL), and the reaction solution was stirred at 100° C. for 19 hours. The reaction solution was left to cool to room temperature. Ethyl acetate and saturated sodium bicarbonate water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane->ethyl acetate) to obtain 134 mg of the title compound. The property values of the compound are as follows.

Workup

waitThe reaction solution was left
temperatureto cool to room temperature
customthe organic layer was separated
dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (elution solvent: heptane->ethyl acetate)

Sources & evidence

ORD record: ord-b77febf5e5fa4e36b64ed573fa83d18b
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07713993B2

Reaction notes

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