Sodium Chloride → HCID 66961869, compound

HRID 1362703Notes

Reaction equation

O1CCOCC1.[F:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH:18]3[CH:16]([O:17]3)[CH2:15]2)=[CH:10][CH:9]=1.[N-:20]=[N+]=[N-].[Na+].[Cl-].[Na+]>C(OCC)(=O)C>[NH2:20][C@@H:18]1[CH2:19][N:14]([C:11]2[CH:12]=[CH:13][C:8]([F:7])=[CH:9][CH:10]=2)[CH2:15][C@H:16]1[OH:17]

Participants

Conditions

Temperature: 100 °C

Procedure

To a 1,4-dioxane (3 mL) solution of 3-(4-fluorophenyl)-6-oxa-3-azabicyclo[3.1.0]hexane (75 mg), an aqueous (1 mL) solution of sodium azide (82 mg) was added, and the reaction solution was agitated at 100° C. for 7 hours. After the reaction solution was allowed to be cooled to room temperature, ethyl acetate and a saturated sodium chloride solution were added to the reaction solution, and the organic layer was partitioned. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. 10% Palladium carbon (48% water content, 10 mg) was added to an ethanol (5 mL) solution of the residue, and the reaction solution was agitated at room temperature under a hydrogen current for 3 hours. 61 mg of the title compound was obtained by carrying out celite filtration of the reaction solution, and condensing the filtrate under reduced pressure. The physical properties of the compound are as follows.

Workup

temperatureto be cooled to room temperature
customthe organic layer was partitioned
dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
addition10% Palladium carbon (48% water content, 10 mg) was added to an ethanol (5 mL) solution of the residue
stirringthe reaction solution was agitated at room temperature under a hydrogen current for 3 hours

Sources & evidence

ORD record: ord-7da6dfdb065e4bc29ddfcb8cb04553bb
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07880009B2

Reaction notes

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