Benzyl 1-(4-fluorophenyl)-2-oxoazepane-3-carboxylate → 1-(4-Fluorophenyl)-2-oxoazepane-3-carboxylic acid

HRID 2241379Notes

Reaction equation

HRID 2241379 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]([C:15]([O:17]CC3C=CC=CC=3)=[O:16])[C:9]2=[O:25])=[CH:4][CH:3]=1>CO.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]([C:15]([OH:17])=[O:16])[C:9]2=[O:25])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 68517020Benzyl 1-(4-fluorophenyl)-2-oxoazepane-3-carboxylate

Product 1

HCID 685156951-(4-Fluorophenyl)-2-oxoazepane-3-carboxylic acidYield 41%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl 1-(4-fluorophenyl)-2-oxoazepane-3-carboxylate (1 g, 3 mmol) and Pd/C (0.1 g, 10% wet) was stirred in MeOH (5 mL) under a H2 atmosphere. After 4 hours, the catalyst was removed by filtration through a pad of silica gel with MeOH. Solvent was evaporated to afford the product (0.3 g, 41% yield) as a white solid. LRMS (APCI pos) m/e 251.8 (M+1).

Workup

  1. customthe catalyst was removed by filtration through a pad of silica gel with MeOH
  2. customSolvent was evaporated

Sources & evidence

ORD record
ord-b22f697b58d54027a90753396d3219d7
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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