[(3R,4R)-4-azidotetrahydrofuran-3-yl]oxy-tert-butyl-dimethyl-silane → (3R,4R)-4-(tert-Butyl(dimethyl)silyl)oxytetrahydrofuran-3-amine

HRID 245063Notes

Reaction equation

HRID 245063 reaction equation
[N:1]([C@@H:4]1[CH2:8][O:7][CH2:6][C@@H:5]1[O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])=[N+]=[N-]>[Pd].C(O)C>[Si:10]([O:9][C@H:5]1[CH2:6][O:7][CH2:8][C@H:4]1[NH2:1])([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Participants

4

Reactant 1

HCID 86693775[(3R,4R)-4-azidotetrahydrofuran-3-yl]oxy-tert-butyl-dimethyl-silane

Product 1

HCID 71151039(3R,4R)-4-(tert-Butyl(dimethyl)silyl)oxytetrahydrofuran-3-amineYield 88.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of [(3R,4R)-4-azidotetrahydrofuran-3-yl]oxy-tert-butyl-dimethyl-silane (1.27 g, 5.22 mmol) and 10% palladium on carbon (25 mg, 0.023 mmol) in ethanol (20 mL) is stirred at room temperature under a hydrogen balloon for 16 h. The reaction is filtered through a pad of diatomaceous earth and the filtrate is concentrated in vacuo to give the title compound as a colorless oil (1.0 g, 88%). LC-ES/MS m/z 218 (M+1).

Workup

  1. filtrationThe reaction is filtered through a pad of diatomaceous earth
  2. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-5927bea749aa4b8e977395af7c8dda26
Source dataset
uspto-grants-2014_02
Patent number
US08658693B2

Reaction notes

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