HCID 178472474, compound → HCID 178472464, compound

HRID 1713898Notes

Reaction equation

HRID 1713898 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([O:8][C@@H:9]2[CH2:14][CH2:13][C@H:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH:6][CH:5]=1)([O-])=O>CCO.C1COCC1.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:8][C@@H:9]2[CH2:14][CH2:13][C@H:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH:20][CH:21]=1

Participants

5

Reactant 1

HCID 178472474HCID 178472474, compound

Product 1

HCID 178472464HCID 178472464, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Palladium (10 wt. %) on carbon (50 mg) was added in one portion to a solution of ethyl cis-4-(4-nitrophenoxy)cyclohexanecarboxylate (0.23 g, 0.78 mmol) in a mixture of EtOH (15 mL) and THF (10 mL) and the reaction mixture was stirred under a hydrogen atmosphere at room temperature for 16 h. The reaction mixture was filtered and then concentrated in vacuo to leave the title compound (0.20 g, 100%) as an oil; 1H NMR (CDCl3) δ 1.23-1.28 (3H, t), 1.55-1.63 (2H, m), 1.68-1.74 (2H, m), 1.93-2.03 (4H, m), 2.34-2.40 (1H, m), 4.10-4.17 (2H, q), 4.26-4.30 (1H, m), 6.60-6.63 (2H, d), 6.73-6.78 (2H, d) MS m/e MH+ 264.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ebacffd20bba4d458fd6b0d8f595fe8b
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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