Azidotrimethylsilane → HCID 59094519, compound

HRID 1168296Notes

Reaction equation

HRID 1168296 reaction equation
[C:1]([C@@H:3]1[C@@H:10]2[C@@H:6]([O:7][C:8]([CH3:12])([CH3:11])[O:9]2)[C@H:5]([O:13][CH3:14])[O:4]1)#[CH:2].C[Si]([N:19]=[N+:20]=[N-:21])(C)C>>[CH3:14][O:13][C@H:5]1[C@@H:6]2[O:7][C:8]([CH3:11])([CH3:12])[O:9][C@@H:10]2[C@@H:3]([C:1]2[CH:2]=[N:21][NH:20][N:19]=2)[O:4]1

Participants

3

Reactant 2

HCID 78378AzidotrimethylsilaneHCID 16070614HCID 16070614, compound

Product 1

HCID 59094519HCID 59094519, compound

Procedure

A solution of (3aR,4R,6R,6aR)-4-ethynyl-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole (Helv. Chim. Acta, 1980, 63(5), 1181) (0.55 g, 2.8 mmol), in trimethylsilylazide (5 ml) was heated at 120 □C. in a teflon lined bomb for 12 hours. The reaction mixture was allowed to cool to room temperature and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane gradually changing to dichloromethane:methanol (98:2 by volume) to give the title compound as a pale brown oil which solidified on standing (0.36 g).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane

Sources & evidence

ORD record
ord-8dcf8ccc8a80445a9206794a6525f305
Source dataset
uspto-grants-2003_09
Patent number
US06624158B2

Reaction notes

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