Methanol → Carbamic acid, N-(4-amino-1-methylcyclohexyl)-, 1,1-dimethylethyl ester

HRID 869243Notes

Reaction equation

HRID 869243 reaction equation
[CH3:1][C:2]1([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.CO.C([O-])=O.[NH4+:22]>[Pd].O>[NH2:22][CH:5]1[CH2:6][CH2:7][C:2]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:1])[CH2:3][CH2:4]1

Participants

6

Reactant 3

HCID 887MethanolHCID 2723923Ammonium formateHCID 21882608tert-Butyl (1-methyl-4-oxocyclohexyl)carbamate

Product 1

HCID 20754832Carbamic acid, N-(4-amino-1-methylcyclohexyl)-, 1,1-dimethylethyl esterYield 92.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

To a mixture of tert-butyl (1-methyl-4-oxocyclohexyl)carbamate (4.00 g) and methanol (50 mL), ammonium formate (10.2 g) and water (5 mL) were added and stirred for 1 hour until they were completely dissolved. Then, 10% palladium on carbon (2.0 g) was added and stirred at room temperature for 65 hours. After insoluble materials were separated by filtration through celite, the solvent was distilled off, and chloroform was added to the resulting residue, followed by drying over anhydrous magnesium sulfate. The solvent was distilled off to give tert-butyl (4-amino-1-methylcyclohexyl)carbamate (3.73 g) as a colorless syrup.

Workup

  1. additionwere added
  2. dissolutionwere completely dissolved
  3. stirringstirred at room temperature for 65 hours
  4. customAfter insoluble materials were separated by filtration through celite
  5. distillationthe solvent was distilled off
  6. additionchloroform was added to the resulting residue
  7. dry with materialby drying over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-2cbd4b36e7ae45179ab9477a99b5524e
Source dataset
uspto-grants-2015_03
Patent number
US08969336B2

Reaction notes

Loading…