Ammonium Chloride → 2-Azido-1-(1,4-dioxaspiro[4.5]decan-8-yl)ethanol

HRID 1896831Notes

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

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-88522d7d2bf34eb6b0dfd000e010fd8f
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518969B2

Reaction notes

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