Water → tert-Butyl [(1S,2R)-2-azidocyclohexyl]carbamate

HRID 546416Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]1OS(C)(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:20]=[N+:21]=[N-:22].[Na+].C(OCC)C.O>CN(C)C=O>[N:20]([C@@H:10]1[CH2:11][CH2:12][CH2:13][CH2:14][C@@H:9]1[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[N+:21]=[N-:22]

Participants

Conditions

Temperature: 60 °C

Procedure

(1S,2S)-1-(tert-Butoxycarbonylamino)-2-methane-sulfonyloxycyclohexane (475 mg) was dissolved in N,N-dimethylformamide (6 ml), sodium azide (156 mg) was added, and the mixture was stirred for 2 hours at 60° C. and then for 24 hours at 80° C. After diethyl ether was added to the reaction mixture to conduct water washing twice, the resultant organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (dichloromethane) to obtain the title compound (184 mg) as a colorless solid.

Workup

waitfor 24 hours at 80° C
dry with materialthe resultant organic layer was dried over anhydrous sodium sulfate
distillationThe solvent was distilled off under reduced pressure
customthe residue was purified by column chromatography on silica gel (dichloromethane)

Sources & evidence

ORD record: ord-20dba5b79e7240598167e99529c97545
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935824B2

Reaction notes

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