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

HRID 546461Notes

Reaction equation

[O:1]1[C@H:7]2[C@@H:2]1[CH2:3][C@H:4]([C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[CH2:5][CH2:6]2.[Cl-].[NH4+].[N-:20]=[N+:21]=[N-:22].[Na+]>CN(C)C=O>[N:20]([C@H:7]1[CH2:6][CH2:5][C@@H:4]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:3][C@@H:2]1[OH:1])=[N+:21]=[N-:22]

Participants

Conditions

Temperature: 70 °C

Procedure

Benzyl (1R*,3S*,4R*)-3,4-epoxycyclohexane-1-carboxylate (52.3 g) was dissolved in N,N-dimethyl-formamide (1000 ml), ammonium chloride (21.9 g) and sodium azide (18.1 g) were added, and the mixture was heated to 70° C. and stirred for 24 hours. The solvent was distilled off under reduced pressure, and water was added to conduct extraction with ethyl acetate. The resultant organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (61.8 g) as a colorless oil.

Workup

distillationThe solvent was distilled off under reduced pressure, and water
additionwas added
extractionextraction with ethyl acetate
washThe resultant organic layer was washed with saturated saline
dry with materialdried over anhydrous magnesium sulfate
distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-49fa912d47a24a1da3b540867dce38a7
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935824B2

Reaction notes

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