HCID 178459277, compound → HCID 178459267, compound

HRID 1445359Notes

Reaction equation

HRID 1445359 reaction equation
C(OC([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([O:15][CH2:16][CH:17]=[CH2:18])[CH2:11][CH2:10]1)=O)(C)(C)C>CO.[C].[Pd]>[CH2:16]([O:15][C@H:12]1[CH2:13][CH2:14][C@H:9]([NH2:8])[CH2:10][CH2:11]1)[CH2:17][CH3:18]

Participants

4

Reactant 1

HCID 178459277HCID 178459277, compound

Product 1

HCID 178459267HCID 178459267, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

In 10 ml of methanol was dissolved 204 mg of N-tert-butoxycarbonyl-trans-4-(2-propen-1-yloxy)cyclohexylamine (the compound of Reference Example 9-11). 44 mg of 10% palladium-carbon was added thereto, and the mixture was stirred under hydrogen atmosphere at normal pressure, at room temperature, for 2 days. The catalyst was removed by filtration and the solvent was removed and the residue was stirred in 2 ml of trifluoroacetic acid for 3 hours. The solvent was removed, and the residue was mixed with an aqueous 10% sodium hydroxide solution, extracted with chloroform and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain 102 mg of trans-4-(propoxy)cyclohexylamine (Reference Example 9-13 in Table 10).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was removed
  3. stirringthe residue was stirred in 2 ml of trifluoroacetic acid for 3 hours
  4. customThe solvent was removed
  5. additionthe residue was mixed with an aqueous 10% sodium hydroxide solution
  6. extractionextracted with chloroform
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-3aa2035ceb494a549b9d88e82513ebc3
Source dataset
uspto-grants-2010_02
Patent number
US07666869B2

Reaction notes

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