HCID 178459268, compound → HCID 178459266, compound

HRID 1483807Notes

Reaction equation

HRID 1483807 reaction equation
C([N:8](CC1C=CC=CC=1)[C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]([OH:18])([CH3:17])[CH3:16])[CH2:11][CH2:10]1)C1C=CC=CC=1>CO.CO.N.[OH-].[OH-].[Pd+2]>[NH2:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]([OH:18])([CH3:16])[CH3:17])[CH2:11][CH2:10]1

Participants

5

Reactant 1

HCID 178459268HCID 178459268, compound

Product 1

HCID 178459266HCID 178459266, compoundYield 375.1%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 21705897Ammonia methanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-(trans-4-(dibenzylamino)cyclohexyl)propan-2-ol (120 g×8, 356 mmol) and Pd(OH)2 (15 g×8) in methanol (1000 mL) and MeOH/NH3 (100 mL) was stirred under H2 (50 psi) at 50° C. for 72 hrs, then the catalyst was removed and the filtrate was concentrated in vacuo and The crude product was chromatographed on silica gel (DCM/MeOH 20:1-DCM/MeOH/NH3 5:4:1) to give the 2-(trans-4-aminocyclohexyl)propan-2-ol as a pale yellow solid (210 g, 47.5% yield).

Workup

  1. customthe catalyst was removed
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe crude product was chromatographed on silica gel (DCM/MeOH 20:1-DCM/MeOH/NH3 5:4:1)

Sources & evidence

ORD record
ord-e96ddabc04fb4a869094413a7112f752
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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