HCID 178418853, compound → HCID 178418966, compound

HRID 2225214Notes

Reaction equation

HRID 2225214 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]1[CH2:13][CH2:12][C@@H:11]([N:14]=[N+]=[N-])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]1[CH2:9][CH2:10][C@@H:11]([NH2:14])[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 178418853HCID 178418853, compound

Product 1

HCID 178418966HCID 178418966, compoundYield 64.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (cis-4-azido-cyclohexyl)-carbamic acid tert-butyl ester (6.3 g, 26 mmol) in MeOH (100 mL) was charged with 5% Pd/C, Degussa style (0.63 g). The sealed flask was evacuated and back-filled with hydrogen; this was repeated three times. The reaction was stirred under 1 atm of H2 for 2 h before being filtered and concentrated in vacuo. The residue was partitioned between Et2O and 1 N HCl. The aqueous phase was basified and extracted with EtOAc (2×). The organic phase was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo to afford (cis-4-amino-cyclohexyl)-carbamic acid tert-butyl ester (3.6 g, 64% yield). MS found: (M+H)+=215.6.

Workup

  1. customThe sealed flask was evacuated
  2. additionback-filled with hydrogen
  3. filtrationbefore being filtered
  4. concentrationconcentrated in vacuo
  5. customThe residue was partitioned between Et2O and 1 N HCl
  6. extractionextracted with EtOAc (2×)
  7. washThe organic phase was washed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c5a6d715282b4b2388bfe1f000ea0f5a
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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