Water → HCID 89525592, compound

HRID 1528153Notes

Reaction equation

C1(P([N:15]=[N+:16]=[N-:17])(C2C=CC=CC=2)=O)C=CC=CC=1.[F:18][CH2:19][C:20]1([CH:24]([C:26]2[O:27][C:28]([CH3:31])=[CH:29][CH:30]=2)O)[CH2:23][O:22][CH2:21]1.N12CCCN=C1CCCCC2.O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[N:15]([CH:24]([C:20]1([CH2:19][F:18])[CH2:23][O:22][CH2:21]1)[C:26]1[O:27][C:28]([CH3:31])=[CH:29][CH:30]=1)=[N+:16]=[N-:17]

Participants

Conditions

Temperature: 0 °C

Procedure

5.80 g (21 mmol, 1.1 eq) of diphenylphosphoryl azide were added dropwise to a solution of 3.83 g (19 mmol, 1 eq) of (3-fluoromethyloxetan-3-yl)-(5-methylfuran-2-yl)methanol in 50 ml of toluene. The reaction medium was cooled to 0° C. and then 3.15 ml (21 mmol, 1.1 eq) of 1,8-diazabicyclo[5.4.0]undec-7-ene were added dropwise. The reaction medium was stirred at ambient temperature for 15 hours. The (heterogeneous) reaction medium was treated with water and with ethyl acetate and then separated by settling out. The organic phase was washed with 1 N hydrochloric acid, dried over magnesium sulfate, filtered and evaporated. The residue was chromatographed on silica gel (column puriFlash IR-50SI/200G, Spot II) eluted with heptane/ethyl acetate (91/9). 2.25 g of 2-[azido-(3-fluoromethyloxetan-3-yl)methyl]-5-methylfuran were obtained in the form of a yellow oil. Yield=53%. TLC SiO2/Heptane:EtOAc (80/20), developing with KMnO4.

Workup

customThe (heterogeneous) reaction medium
customseparated
washThe organic phase was washed with 1 N hydrochloric acid
dry with materialdried over magnesium sulfate
filtrationfiltered
customevaporated
customThe residue was chromatographed on silica gel (column puriFlash IR-50SI/200G, Spot II)
washeluted with heptane/ethyl acetate (91/9)

Sources & evidence

ORD record: ord-a9551668c74740da9528a91b370580c7
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090596B2

Reaction notes

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