Ethyl Acetate → HCID 178477568, compound

HRID 853121Notes

Reaction equation

HRID 853121 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]([C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1)([O:8][Si:9]([CH2:14][CH3:15])([CH2:12][CH3:13])[CH2:10][CH3:11])[C:4]([F:7])([F:6])[F:5].[OH-].[Na+].CCOC(C)=O.CCOC(C)=O.CO>CC(O)=O.[Pt]>[F:24][C:2]([F:1])([F:23])[C:3]([C@@H:16]1[CH2:21][CH2:20][C@H:19]([NH2:22])[CH2:18][CH2:17]1)([O:8][Si:9]([CH2:12][CH3:13])([CH2:10][CH3:11])[CH2:14][CH3:15])[C:4]([F:7])([F:6])[F:5].[F:24][C:2]([F:1])([F:23])[C:3]([C@H:16]1[CH2:21][CH2:20][C@H:19]([NH2:22])[CH2:18][CH2:17]1)([O:8][Si:9]([CH2:12][CH3:13])([CH2:10][CH3:11])[CH2:14][CH3:15])[C:4]([F:7])([F:6])[F:5]

Participants

8

Reactant 4

HCID 8857Ethyl Acetate2×HCID 14798Sodium HydroxideHCID 21584119Ethylacetate methanolHCID 87824967HCID 87824967, compound

Product 2

HCID 178477568HCID 178477568, compoundYield 37%HCID 178477569HCID 178477569, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 5 g (13.4 mmol) of 4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-phenylamine in 150 mL of AcOH was treated with 2.5 g of Pt/C (10%) and hydrogenated for 72 hrs at atmospheric pressure under intense stirring. Filtration and evaporation of the solvent gave a yellow semisolid that was distributed between a 1M aqueous solution of NaOH and EtOAc. The combined organic phases were dried over Na2SO4 and evaporated to yield 4 g of crude product. Chromatography on silica gel with EtOAc and then EtOAc/MeOH 10:1 gave ca. 1.9 g (37%) of cis-4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-cyclohexylamine and ca. 1.9 g (37%) trans-4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-cyclohexylamine as a light yellow oil, MS: 380 (M+H)+.

Workup

  1. filtrationFiltration and evaporation of the solvent
  2. customgave a yellow semisolid
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. customevaporated
  5. customto yield 4 g of crude product

Sources & evidence

ORD record
ord-014ba6b5f2bd4738ae9da38fc7812b02
Source dataset
uspto-grants-2007_08
Patent number
US07253282B2

Reaction notes

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