(1R,2S)-[2-({[3-(4-fluoro-phenyl)-propyl]-methyl-amino}-methyl)-cyclohexyl]-carbamic Acid Benzyl Ester → (1R,2S)-2-({[3-(4-fluorophenyl)-propyl]-methyl-amino}-methyl)-cyclohexylamine

HRID 1592327Notes

Reaction equation

HRID 1592327 reaction equation
C(OC(=O)[NH:10][C@@H:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]1[CH2:17][N:18]([CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)[CH3:19])C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[F:29][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][CH2:21][CH2:20][N:18]([CH2:17][C@@H:12]2[CH2:13][CH2:14][CH2:15][CH2:16][C@H:11]2[NH2:10])[CH3:19])=[CH:28][CH:27]=1

Participants

4

Reactant 1

HCID 69424744(1R,2S)-[2-({[3-(4-fluoro-phenyl)-propyl]-methyl-amino}-methyl)-cyclohexyl]-carbamic Acid Benzyl Ester

Product 1

HCID 69426356(1R,2S)-2-({[3-(4-fluorophenyl)-propyl]-methyl-amino}-methyl)-cyclohexylamine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of (1R,2S)-[2-({[3-(4-fluoro-phenyl)-propyl]-methyl-amino}-methyl)-cyclohexyl]-carbamic acid benzyl ester (400 mg, 970 μM) and 20% palladium hydroxide on charcoal (Pearlman's catalyst, 200 mg) in methanol (25 mL) was shaken in a pressure bottle under a hydrogen atmosphere (55 psig) for 16.5 hours. The mixture was filtered and the solid was washed with methanol. The combined filtrates were concentrated under vacuum to provide a tan viscous oil (268 mg, quantitative), used without further purification.

Workup

  1. filtrationThe mixture was filtered
  2. washthe solid was washed with methanol
  3. concentrationThe combined filtrates were concentrated under vacuum
  4. customto provide a tan viscous oil (268 mg, quantitative)
  5. customused without further purification

Sources & evidence

ORD record
ord-67ea9cb5bfa848e28ddcba112c638f28
Source dataset
uspto-grants-2007_11
Patent number
US07291744B2

Reaction notes

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