(1S,3S,4S)-4-azido-3-hydroxy-cyclohexanecarboxylic acid amide → HCID 45083256, compound

HRID 723538Notes

Reaction equation

HRID 723538 reaction equation
[N:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]([NH2:12])=[O:11])[CH2:6][C@@H:5]1[OH:13])=[N+]=[N-]>CO.[Pd]>[NH2:1][C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]([NH2:12])=[O:11])[CH2:6][C@@H:5]1[OH:13]

Participants

4

Reactant 1

HCID 86612935(1S,3S,4S)-4-azido-3-hydroxy-cyclohexanecarboxylic acid amide

Product 1

HCID 45083256HCID 45083256, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To (1S,3S,4S)-4-azido-3-hydroxy-cyclohexanecarboxylic acid amide (352c) (760 mg, 4.13 mmol) in MeOH (30 mL) was added Pd/C (10%, 500 mg), and the mixture hydrogenated under atmospheric pressure for 18 h. On completion of reaction the mixture was filtered through Celite®, the filter pad washed with MeOH, and the combined organic solutions concentrated in vacuo to give a white solid in quantitative yield;

Workup

  1. customOn completion of reaction the mixture
  2. filtrationwas filtered through Celite®
  3. washthe filter pad washed with MeOH
  4. concentrationthe combined organic solutions concentrated in vacuo
  5. customto give a white solid in quantitative yield

Sources & evidence

ORD record
ord-23e404d58528429ca5b362e0173d60bc
Source dataset
uspto-grants-2006_11
Patent number
US07141564B2

Reaction notes

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