Ethyl (1S,3R,4S)-4-azido-3-[(tert-butoxycarbonyl)amino]cyclohexane-1-carboxylate → Ethyl (1S,3R,4S)-4-amino-3-[(tert-butoxycarbonyl)amino]cyclohexane-1-carboxylate

HRID 546458Notes

Reaction equation

HRID 546458 reaction equation
[N:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6][C@H:5]1[NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[N+]=[N-].[H][H]>C(O)C.C(OCC)(=O)C.[Pd]>[C:19]([O:18][C:16]([NH:15][C@@H:5]1[CH2:6][C@@H:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:8][CH2:9][C@@H:4]1[NH2:1])=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 2

HCID 57416168Ethyl (1S,3R,4S)-4-azido-3-[(tert-butoxycarbonyl)amino]cyclohexane-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 16005245Ethyl (1S,3R,4S)-4-amino-3-[(tert-butoxycarbonyl)amino]cyclohexane-1-carboxylateYield 114.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl (1S,3R,4S)-4-azido-3-(tert-butoxy-carbonylamino)cyclohexane-1-carboxylate (4.0 g) was dissolved in a mixed solvent of ethanol (150 ml) and ethyl acetate (150 ml), and 5% palladium on carbon (0.5 g) was added to stir the mixture at room temperature for 17 hours in a hydrogen atmosphere. After insoluble matter was removed by filtration, the solvent was distilled off under reduced pressure to obtain the title compound (4.2 g) as a pale yellow oil.

Workup

  1. additionwas added
  2. customAfter insoluble matter was removed by filtration
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-87d687248d0e4f7ead999c48af232980
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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