Dichloromethane → HCID 21291621, compound

HRID 1749391Notes

Reaction equation

HRID 1749391 reaction equation
C(OC(=O)[NH:10][CH:11]1[CH2:16][CH2:15][CH:14]([OH:17])[C:13]([CH3:19])([CH3:18])[CH2:12]1)C1C=CC=CC=1.C(Cl)Cl>[Pd].CO>[NH2:10][CH:11]1[CH2:16][CH2:15][CH:14]([OH:17])[C:13]([CH3:19])([CH3:18])[CH2:12]1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 131733576HCID 131733576, compound

Product 1

HCID 21291621HCID 21291621, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

Benzyl-4-hydroxy-3,3-dimethylcyclohexylcarbamate (peak 1) (1.0 equiv.) and palladium on carbon (10%) in MeOH (0.37 M) was stirred at room temperature under hydrogen balloon overnight. TLC (DCM:MeOH=10:1) showed that the reaction was completed. The mixture was filtered through a celite pad and evaporation of the solvents under reduced pressure provided 4-amino-2,2-dimethylcyclohexanol (95% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm) 3.70 (s, 2H), 3.16 (s, 1H), 2.65-2.71 (m, 1H), 1.18-1.65 (m, 6H), 0.83 (m, 6H).

Workup

  1. filtrationThe mixture was filtered through a celite pad and evaporation of the solvents under reduced pressure

Sources & evidence

ORD record
ord-89c597f409c645bab86c5fea39628922
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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