Reaction #77726

ord-21c48cd3a7d74f6fadbd7dcc8a5cfc32

Reaction equation

CC(=O)OC[C@H]1O[C@H](OC(C)=O)[C@H](N=[N+]=[N-])[C@@H](OC(C)=O)[C@@H]1OC(C)=O
1,3,4,6-tetra-o-acetyl-2-azido-2-deoxy-alpha-D-glucopyranose
→
CC(=O)OC[C@H]1O[C@H](OC(C)=O)[C@H](N)[C@@H](OC(C)=O)[C@@H]1OC(C)=O
amine
Yield 101.5%
CC(=O)OC[C@H]1O[C@H](OC(C)=O)[C@H](N)[C@@H](OC(C)=O)[C@@H]1OC(C)=O
1,3,4,6-TETRA-O-ACETYL-2-AMINO-2-DEOXY-alpha-D-GLUCOPYRANOSE
Yield 101.5%

Reactants

CC(=O)OC[C@H]1O[C@H](OC(C)=O)[C@H](N=[N+]=[N-])[C@@H](OC(C)=O)[C@@H]1OC(C)=O
1,3,4,6-tetra-o-acetyl-2-azido-2-deoxy-alpha-D-glucopyranose

Reagents

[Pd]
Pd/C

Solvents

CCOC(C)=O
EtOAc

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    FiltrationThe mixture was filtered through a pad of Celite®
  2. 2
    Washthe pad was washed with EtOAc (20 mL)
  3. 3
    OtherThe solution was evaporated

Procedure

To a solution of 1,3,4,6-tetra-o-acetyl-2-azido-2-deoxy-alpha-D-glucopyranose (TCI-US) (300 mg, 0.80 mmol) in 25 mL of EtOAc was added 180 mg of 10% Pd/C. This solution was stirred under an atmosphere of hydrogen gas (1 atm) for 3 hours. The mixture was filtered through a pad of Celite® and the pad was washed with EtOAc (20 mL). The solution was evaporated to afford the desired amine 149 (282 mg, 100%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06706740B2uspto-grants-2004_03