Ammonium Chloride → 2-Azido-1-(1,4-dioxaspiro[4.5]decan-8-yl)ethanol
Reaction equation
[O:1]1[CH2:3][CH:2]1[CH:4]1[CH2:13][CH2:12][C:7]2([O:11][CH2:10][CH2:9][O:8]2)[CH2:6][CH2:5]1.[N-:14]=[N+:15]=[N-:16].[Na+].[Cl-].[NH4+]>CO>[N:14]([CH2:3][CH:2]([CH:4]1[CH2:13][CH2:12][C:7]2([O:11][CH2:10][CH2:9][O:8]2)[CH2:6][CH2:5]1)[OH:1])=[N+:15]=[N-:16]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 8-(oxiran-2-yl)-1,4-dioxaspiro[4.5]decane (205 mg, 1.11 mmol), prepared in the previous step, in methanol (5 mL) water (0.5 mL) was added sodium azide (361 mg, 5.56 mmol) and ammonium chloride (119 mg, 2.22 mmol). The mixture was stirred, heating to 80° C. under argon overnight and then cooled to ambient temperature and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, ether) to afford the product.
Workup
- temperaturecooled to ambient temperature
- concentrationconcentrated in vacuo
- customThe residue was purified by flash chromatography (silica gel, ether)
- customto afford the product
Sources & evidence
- ORD record
- ord-f1db06584f2d4a19a371a7b851d40321
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09062048B2
Reaction notes
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