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

HRID 723535Notes

Reaction equation

HRID 723535 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 salt

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To (1R,3R,4R)-4-azido-3-hydroxy-cyclohexanecarboxylic acid amide (351c) (765 mg, 4.15 mmol) in MeOH/AcOH (9:1, 30 mL) was added Pd/C (10%, 300 mg), and the mixture hydrogenated under atmospheric pressure for 22 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-0a9d8d8b1cad4e62b23ed479d46b224c
Source dataset
uspto-grants-2006_11
Patent number
US07141564B2

Reaction notes

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