HCID 178477574, compound → HCID 178477570, compound

HRID 853134Notes

Reaction equation

HRID 853134 reaction equation
C([N:8]([CH2:32][CH:33]1[CH2:35][CH2:34]1)[C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]([O:24][Si:25]([CH2:30][CH3:31])([CH2:28][CH3:29])[CH2:26][CH3:27])([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17])[CH2:11][CH2:10]1)C1C=CC=CC=1>C(O)(=O)C.[Pd]>[CH:33]1([CH2:32][NH:8][C@H:9]2[CH2:10][CH2:11][C@H:12]([C:15]([O:24][Si:25]([CH2:28][CH3:29])([CH2:30][CH3:31])[CH2:26][CH3:27])([C:16]([F:17])([F:18])[F:19])[C:20]([F:23])([F:22])[F:21])[CH2:13][CH2:14]2)[CH2:34][CH2:35]1

Participants

4

Reactant 1

HCID 178477574HCID 178477574, compound

Product 1

HCID 178477570HCID 178477570, compoundYield 89.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

1 g (ca 2.0 mmol) of crude trans benzyl-cyclopropylmethyl-[4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-cyclohexyl]-amine was dissolved in 50 mL of acetic acid, treated with 300 mg of Pd/C (10%) and hydrogenated overnight at atmospheric pressure under intense stirring. Filtration and evaporation of the solvent gave 775 mg (ca 82%) of crude trans cyclopropylmethyl-[4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-cyclohexyl]-amine as a yellow oil, MS: 434 (M+H)+.

Workup

  1. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-d9fc47315ad24028a1bfccccf15a67f4
Source dataset
uspto-grants-2007_08
Patent number
US07253282B2

Reaction notes

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