Lithium azide → 2-(2-(((1,1-Dimethylethyl)dimethylsilyl)oxy)ethyl)-3-(((1,1-dimethylethyl)dimethylsilyl)oxymethyl)-1-azidocyclobutane

HRID 5970

Reaction equation

HRID 5970 reaction equation
[CH3:1][C:2]([Si:5]([CH3:28])([CH3:27])[O:6][CH2:7][CH2:8][C:9]1(OS(C)(=O)=O)[CH2:12][CH:11](CO[Si](C(C)(C)C)(C)C)[CH2:10]1)([CH3:4])[CH3:3].[N-:29]=[N+:30]=[N-:31].[Li+]>CN(C=O)C>[CH3:4][C:2]([Si:5]([CH3:27])([CH3:28])[O:6][CH2:7][CH2:8][CH:9]1[CH:10]([CH2:7][O:6][Si:5]([C:2]([CH3:4])([CH3:3])[CH3:1])([CH3:28])[CH3:27])[CH2:11][CH:12]1[N:29]=[N+:30]=[N-:31])([CH3:1])[CH3:3]

Participants

4

Reactant 2

HCID 88163Lithium azideHCID 867472362-(((1,1-Dimethylethyl)dimethylsilyl)oxy)ethyl-3-(((1,1-dimethylethyl)dimethyl-silyl)oxymethyl)-1-O-methanesulfonylcyclobutanol

Product 1

HCID 197942502-(2-(((1,1-Dimethylethyl)dimethylsilyl)oxy)ethyl)-3-(((1,1-dimethylethyl)dimethylsilyl)oxymethyl)-1-azidocyclobutaneYield 146.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2-(2-(((1,1-Dimethylethyl)dimethylsilyl)oxy)ethyl-3-(((1,1-dimethylethyl)dimethyl-silyl)oxymethyl)-1-O-methanesulfonylcyclobutanol (180 mg, 0.41 mmol) was mixed with 200 mg (4.1 mmol) of lithium azide in 4 mL of DMF. The reaction mixture was heated at 80° C. for 2 h then concentrated in vacuo. The residue was purified on a silica gel column eluted with 5% ethyl acetate in hexane to give 120 mg (73% yield) of the title compound; MS DCI-NH3M/Z: 400 (M+H)+, 417 (M+NH4)+.

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was purified on a silica gel column
  3. washeluted with 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-d5f0c7a4ccb444f19b70b9728ca3aa5e
Source dataset
uspto-grants-1993_09
Patent number
US05246931

Linked notes

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