tert-butyl (1S,2S,4S)-4-(dibenzylamino)-2-methylcyclohexylcarbamate tert-butyl (1R,2R,4R)-4-(dibenzylamino)-2-methylcyclohexylcarbamate → tert-butyl (1S,2S,4S)-4-amino-2-methylcyclohexylcarbamate tert-butyl (1R,2R,4R)-4-amino-2-methylcyclohexylcarbamate

HRID 1963909Notes

Reaction equation

HRID 1963909 reaction equation
C([N:8](CC1C=CC=CC=1)[C@H:9]1[CH2:14][CH2:13][C@H:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C@@H:11]([CH3:23])[CH2:10]1)C1C=CC=CC=1.C([N:38](CC1C=CC=CC=1)[C@@H:39]1[CH2:44][CH2:43][C@@H:42]([NH:45][C:46](=[O:52])[O:47][C:48]([CH3:51])([CH3:50])[CH3:49])[C@H:41]([CH3:53])[CH2:40]1)C1C=CC=CC=1>[OH-].[OH-].[Pd+2].CCO>[NH2:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:19])[CH3:21])[C@@H:11]([CH3:23])[CH2:10]1.[NH2:38][C@@H:39]1[CH2:44][CH2:43][C@@H:42]([NH:45][C:46](=[O:52])[O:47][C:48]([CH3:50])([CH3:49])[CH3:51])[C@H:41]([CH3:53])[CH2:40]1

Participants

4

Reactant 1

HCID 86650621tert-butyl (1S,2S,4S)-4-(dibenzylamino)-2-methylcyclohexylcarbamate tert-butyl (1R,2R,4R)-4-(dibenzylamino)-2-methylcyclohexylcarbamate

Product 1

HCID 86650623tert-butyl (1S,2S,4S)-4-amino-2-methylcyclohexylcarbamate tert-butyl (1R,2R,4R)-4-amino-2-methylcyclohexylcarbamate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of tert-butyl (1S,2S,4S)-4-(dibenzylamino)-2-methylcyclohexylcarbamate/tert-butyl (1R,2R,4R)-4-(dibenzylamino)-2-methylcyclohexylcarbamate (750 mg, 1.836 mmol) and Pearlman's catalyst (290 mg, 2.73 mmol) in EtOH (35 mL) was hydrogenated in a steel bomb under H2-atmosphere (pressure ˜75 psi) for 16 hr. The steel bomb was flushed with Argon, Celite and methanol were added. The mixture was filtered and concentrated in vacuo. The white resulting residue was dissolved in acetonitrile/water (1:1) and lyophilized giving crude tert-butyl (1S,2S,4S)-4-amino-2-methylcyclohexylcarbamate/tert-butyl (1R,2R,4R)-4-amino-2-methylcyclohexylcarbamate, which was directly used in the next step without further purification. Yield: 412 mg. LCMS (m/z): 173.2/229.3 [M+H]+; Retention time=0.54 min.

Workup

  1. customfor 16 hr
  2. customThe steel bomb was flushed with Argon, Celite and methanol
  3. additionwere added
  4. filtrationThe mixture was filtered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe white resulting residue was dissolved in acetonitrile/water (1:1)

Sources & evidence

ORD record
ord-f2acfe32f30141b3adcd034e383b37d0
Source dataset
uspto-grants-2013_04
Patent number
US08415381B2

Reaction notes

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