(1S,3R)-3-(dibenzylamino)-1-methylcyclohexanol → HCID 86676339, compound

HRID 2280732Notes

Reaction equation

HRID 2280732 reaction equation
C([N:8](CC1C=CC=CC=1)[C@@H:9]1[CH2:14][CH2:13][CH2:12][C@:11]([CH3:16])([OH:15])[CH2:10]1)C1C=CC=CC=1.[H][H]>C(O)C.[OH-].[OH-].[Pd+2]>[NH2:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][C@@:11]([CH3:16])([OH:15])[CH2:10]1

Participants

5

Reactant 2

HCID 71237246(1S,3R)-3-(dibenzylamino)-1-methylcyclohexanolHCID 178418361HCID 178418361, compound

Product 1

HCID 86676339HCID 86676339, compoundYield 62.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of (1S,3R)-3-(dibenzylamino)-1-methylcyclohexanol (5.0 g, 16.16 mmol) in ethanol (150 mL) was treated with palladium hydroxide on carbon and stirred under a balloon filled with hydrogen gas overnight. Upon completion of the reaction as indicated by LCMS the reaction mixture was filtered through a pad of celite and the filtrate concentrated to yield (1R,3R)-3-amino-1-methylcyclohexanol (1.3 g, 62%) as a thick yellow oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.87 (br. s., 1H), 1.64-1.74 (m, 1H), 1.47-1.59 (m, 2H), 1.21-1.40 (m, 4H), 1.11-1.20 (m, 1H), 1.02 (s, 3H); MS (ESI) m/z 130.2 [M+1]+.

Workup

  1. customUpon completion of the reaction
  2. filtrationwas filtered through a pad of celite
  3. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-8f28cd05ed034920ac2dc807d156b190
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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