Ammonium Chloride → Ethyl (1S,3R,4R)-3-azido-4-hydroxycyclohexane-1-carboxylate

HRID 546456Notes

Reaction equation

[O:1]1[C@H:7]2[C@@H:2]1[CH2:3][C@@H:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:5][CH2:6]2.[Cl-].[NH4+].[N-:15]=[N+:16]=[N-:17].[Na+]>CN(C)C=O>[N:15]([C@H:2]1[C@H:7]([OH:1])[CH2:6][CH2:5][C@H:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:3]1)=[N+:16]=[N-:17]

Participants

Conditions

Temperature: 75 °C

Procedure

Ethyl (1S,3S,4R)-3,4-epoxycyclohexane-1-carboxylate (41 g) was dissolved in N,N-dimethyl-formamide (300 ml), ammonium chloride (19.3 g) and sodium azide (23.5 g) were successively added at room temperature, and the mixture was then stirred at 75° C. for 13 hours. The reaction mixture was filtered, the filtrate was concentrated to distill off 400 ml of the solvent, the product captured by the filter was put in the residue, and water was added to dissolve the collected product. The solution was extracted with ethyl acetate. The resultant organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (51.5 g) as an oil.

Workup

filtrationThe reaction mixture was filtered
concentrationthe filtrate was concentrated
distillationto distill off 400 ml of the solvent
additionwas added
dissolutionto dissolve the collected product
extractionThe solution was extracted with ethyl acetate
washThe resultant organic layer was washed with water and saturated saline
dry with materialdried over anhydrous magnesium sulfate
distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-21bd43fc714140d9964d864c81ca0bd9
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935824B2

Reaction notes

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