Sodium Hydroxide → tert-Butyl N-(2-{[5-(trifluoromethyl)pyridin-2-yl]methyl}cyclopentyl)carbamate

HRID 1750534Notes

Reaction equation

HRID 1750534 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[CH:5][C:6](/[CH:9]=[C:10]2/[CH:11]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:12][CH2:13][CH2:14]/2)=[N:7][CH:8]=1.[OH-].[Na+].[H][H]>CO.[Pd]>[F:24][C:2]([F:1])([F:23])[C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH:10]2[CH2:14][CH2:13][CH2:12][CH:11]2[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:21])[CH3:19])=[N:7][CH:8]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 118308075tert-Butyl N-[(2E)-2-{[5-(trifluoromethyl)pyridin-2-yl]methylidene}cyclopentyl]carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 118308149tert-Butyl N-(2-{[5-(trifluoromethyl)pyridin-2-yl]methyl}cyclopentyl)carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl N-[(2E)-2-{[5-(trifluoromethyl)pyridin-2-yl]methylidene}cyclopentyl]carbamate (1.5 g, 4.38 mmol) in methanol (5 ml) was added palladium on carbon (10% wt, 50% wet, 300 mg) and 2M NaOH (5 ml). The resulting reaction was stirred under a balloon of hydrogen gas for 2 hours. The reaction was filtered through diatomaceous earth (commercially sold under the trade mark “Celite”) and concentrated in vacuo to afford the title compound. The resulting residue was purified by column chromatography (silica, 0-70% ethyl acetate/n-hexane) to afford the title compound.

Workup

  1. customThe resulting reaction
  2. filtrationThe reaction was filtered through diatomaceous earth (
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7fe2798a88a346f387fccdff2ea54d91
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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