Sodium Azide → (S)-2-Azido-2-(6-(trifluoromethyl)pyridin-3-yl)ethanol

HRID 1845122Notes

Reaction equation

[O:1]1[CH2:3][C@H:2]1[C:4]1[CH:5]=[CH:6][C:7]([C:10]([F:13])([F:12])[F:11])=[N:8][CH:9]=1.Cl([O-])(=O)(=O)=O.[Li+].[N-:20]=[N+:21]=[N-:22].[Na+]>C(#N)C>[N:20]([C@@H:2]([C:4]1[CH:9]=[N:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][CH:5]=1)[CH2:3][OH:1])=[N+:21]=[N-:22]

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of (R)-5-(oxiran-2-yl)-2-(trifluoromethyl)pyridine (2.72 g, 14.4 mmol) in acetonitrile (200 mL) were added lithium perchlorate (20 g, 0.19 mol) and sodium azide (3.7 g, 57 mmol). The mixture was stirred at 60° C. overnight and TLC indicated completion of the reaction. After cooling, the mixture was filtered through Celite and the filtrate was concentrated. The residue was treated with water and extracted with EtOAc. The combined organic layers were dried, and concentrated. The residue was purified by silica gel column to afford the title compound.

Workup

customcompletion of the reaction
temperatureAfter cooling
filtrationthe mixture was filtered through Celite
concentrationthe filtrate was concentrated
additionThe residue was treated with water
extractionextracted with EtOAc
customThe combined organic layers were dried
concentrationconcentrated
customThe residue was purified by silica gel column

Sources & evidence

ORD record: ord-682a5483668f44a180b39332bf9f274c
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946439B2

Reaction notes

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