HCID 86591976, compound → HCID 58779883, compound

HRID 729206Notes

Reaction equation

HRID 729206 reaction equation
[N:1]([CH2:4][C@@H:5]1[O:14][C@@:8]2([C:15]([O:17][CH3:18])=[O:16])[O:9][C:10]([CH3:13])([CH3:12])[O:11][CH:7]2[C@@H:6]1[OH:19])=[N+]=[N-]>CO>[NH2:1][CH2:4][C@@H:5]1[O:14][C@:8]2([C:15]([O:17][CH3:18])=[O:16])[C@@H:7]([O:11][C:10]([CH3:12])([CH3:13])[O:9]2)[C@@H:6]1[OH:19]

Participants

3

Reactant 1

HCID 86591976HCID 86591976, compound

Product 1

HCID 58779883HCID 58779883, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 15 (1.0 g, 3.7 mmol) in MeOH (30 mL) were added aqueous HCl (conc., 0.32 mL) and palladium, 10 wt. % (dry basis) on activated carbon (wet, Degussa type E101 NE/W, 307 mg, Aldrich). It was hydrogenated at 22 psi for 0.5 h. The mixture was filtered through a Celite cake and the solvent evaporated to dryness. Product 16 was obtained as an off white solid (1.0 g; yield 91.0%).

Workup

  1. dry with materialHCl (conc., 0.32 mL) and palladium, 10 wt. % (dry basis) on activated carbon (wet, Degussa type E101 NE/W, 307 mg, Aldrich)
  2. filtrationThe mixture was filtered through a Celite cake
  3. customthe solvent evaporated to dryness

Sources & evidence

ORD record
ord-e9724b2ce2c64a91add195488e517d53
Source dataset
uspto-grants-2009_09
Patent number
US07582280B2

Reaction notes

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