Ethanol → HCID 58842268, compound

HRID 1270445Notes

Reaction equation

HRID 1270445 reaction equation
[CH2:1]1[C@@H:3]([NH2:4])[C@@H:2]1[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:11][CH2:12][OH:13]>[Pd]>[C:5]1([CH2:2][CH2:1][CH2:3][NH:4][C:12]([C:11]2([CH:8]([CH3:9])[CH3:7])[CH2:6][CH2:5][CH2:2][CH2:1][CH2:3]2)=[O:13])[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 19493(1R,2S)-Tranylcypromine

Product 1

HCID 58842268HCID 58842268, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Compound 1 (33 mg, 0.12 mmol) and 10% Pd on carbon (30 mg), in EtOH (1 mL) was stirred under hydrogen for 18 h. The reaction mixture was filtered over celite and concentrated to give 1-isopropyl-cyclohexanecarboxylic acid (3-phenyl-propyl)-amide (33 mg, 100%) as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ (ppm) 0.86 (6H, d, J=6.8 Hz), 1.00–1.40 (5H, m), 1.50–1.65 (4H, m), 1.80–1.90 (4H, m), 2.67 (2H, t, J=7.5 Hz), 3.33–3.48 (2H, m), 5.59 (1H, s), 7.17–7.31 (5H, m). Mass Spec [M+H]+=288.

Workup

  1. filtrationThe reaction mixture was filtered over celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-1be954d2fd294af1ae1dcf6ae48796a9
Source dataset
uspto-grants-2007_04
Patent number
US07202253B2

Reaction notes

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