Oxetane → [3-(Azidomethyl)oxetan-3-yl]methanol

HRID 2395866Notes

Reaction equation

HRID 2395866 reaction equation
O1CCC1.Br[CH2:6][C:7]1([CH2:11][OH:12])[CH2:10][O:9][CH2:8]1.[N-:13]=[N+:14]=[N-:15].[Na+]>CC(C)=O.CN(C)C=O>[N:13]([CH2:6][C:7]1([CH2:11][OH:12])[CH2:10][O:9][CH2:8]1)=[N+:14]=[N-:15]

Participants

6

Reactant 3

HCID 10423Oxetane2×HCID 33557Sodium AzideHCID 529264[3-(Bromomethyl)oxetan-3-yl]methanol2×

Product 1

HCID 22404019[3-(Azidomethyl)oxetan-3-yl]methanol

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

The oxetane of the present invention has the formula: ##STR1## The oxetane of Formula I, 3-azidomethyl-3-nitratomethyloxetane (ANMO), is synthesized using 3-bromomethyl-3-hydroxymethyl oxetane (BMHMO) as the starting material. Reaction of 3-bromomethyl-3-hydroxymethyloxetane with sodium azide (NAN3) in acetone or dimethylformamide (DMF) gives the corresponding 3-azidomethyl-3-hydroxymethyloxetane in essentially quantitative yield. Subsequent reaction of 3-azidomethyl-3-hydroxymethyloxetane with acetyl nitrate gives the oxetane AMNO.

Sources & evidence

ORD record
ord-06daef1b8ab0462bb713c6a52335b318
Source dataset
uspto-grants-1996_02
Patent number
US05489700

Reaction notes

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