HCID 178471701, compound → HCID 178471699, compound

HRID 272253Notes

Reaction equation

HRID 272253 reaction equation
C([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[CH:29]=[CH:28][C:18]([O:19][C:20]([CH3:27])([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)C1C=CC=CC=1>C(O)C.[Pd]>[NH2:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[CH:16]=[CH:17][C:18]([O:19][C:20]([CH3:26])([CH3:27])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:28][CH:29]=2)[CH2:11][CH2:10]1

Participants

4

Reactant 1

HCID 178471701HCID 178471701, compound

Product 1

HCID 178471699HCID 178471699, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1.9 g of ethyl trans-2-{4-[4-(benzylamino)cyclohexyl]phenoxy}-2,2-dimethylacetate in the base form (4.8 mmol) and of 0.1 g of 10% palladium-on-charcoal in ethanol (75 ml) is placed under hydrogen atmosphere at 40° C. and stirred for 7 h. The reaction mixture is filtered through celite. The solvent is evaporated under reduced pressure and ethyl trans-2-[4-(4-aminocyclohexyl)phenoxy]-2,2-dimethylacetate is obtained (0.660 g) in the form of a yellow oil which is dissolved in ethanol (5 ml). The solution is acidified with a solution (9N) of HCl in ethanol and the solid thus obtained is filtered off (0.530 g, 72%). Melting point: 240-242.

Workup

  1. customis placed under hydrogen atmosphere at 40° C.
  2. filtrationThe reaction mixture is filtered through celite
  3. customThe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-0170956a5f834f3fb4331f9c7f834d3b
Source dataset
uspto-grants-2008_11
Patent number
US07453010B2

Reaction notes

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