Acetic acid methanol → (1R,3R,4R)-4-amino-3-hydroxy-cyclohexanecarboxylic acid amide, acetate salt

HRID 1437336Notes

Reaction equation

HRID 1437336 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.[CH3:16][C:17]([OH:19])=[O:18]>[Pd]>[C:17]([OH:19])(=[O:18])[CH3:16].[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 2

HCID 10129899Acetic acid methanolHCID 58743879(1R,3R,4R)-4-Azido-3-hydroxy-cyclohexanecarboxylic acid amide

Product 1

HCID 131726103(1R,3R,4R)-4-amino-3-hydroxy-cyclohexanecarboxylic acid amide, acetate saltYield 100%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To (1R,3R,4R)-4-azido-3-hydroxy-cyclohexanecarboxylic acid amide (c) (765 mg, 4.15 mmol) in MeOH/AcOH (9:1, 30 mL) was added Pd/C (10%, 300 mg), and the mixture stirred under hydrogen at atmospheric pressure for 22 hours. The mixture was filtered through Celite®, the residue washed with MeOH, and the combined organic extracts concentrated in vacuo to give a white solid (905 mg, 100%).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. washthe residue washed with MeOH
  3. concentrationthe combined organic extracts concentrated in vacuo

Sources & evidence

ORD record
ord-39c9bdaf4a4f470d9140d91708b2cedb
Source dataset
uspto-grants-2009_11
Patent number
US07622481B2

Reaction notes

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