1,8-Diazabicyclo(5.4.0)undec-7-ene → Trifluoromethanesulfonic acid 5-azido-5,6,7,8-tetrahydronaphthalen-2-yl ester

HRID 1269457Notes

Reaction equation

O[CH:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([O:12][S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])[CH:5]=[CH:4][C:3]1=2.C1C=CC(P([N:34]=[N+:35]=[N-:36])(C2C=CC=CC=2)=O)=CC=1.C1CCN2C(=NCCC2)CC1>C1COCC1>[N:34]([CH:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([O:12][S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])[CH:5]=[CH:4][C:3]1=2)=[N+:35]=[N-:36]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of trifluoro-methanesulfonic acid 5-hydroxy-5,6,7,8-tetrahydro-naphthalen-2-yl ester (11.2 g, 37.9 mmol, 1.0 eq) in THF (150 mL) at RT was added DPPA (Aldrich, 11.1 mL, 51.6 mmol, 1.36 eq). The resulting mixture was cooled to 0° C., then DBU (Aldrich, 7.7 mL, 51.6 mmol, 1.36 eq) was added slowly through a syringe. The reaction was warmed to RT and stirred over the weekend. The mixture was concentrated in vacuo. The residue was dissolved in EtOAc (400 mL), washed with saturated NH4Cl (twice), water, and brine, dried over Na2SO4, and concentrated in vacuo. The crude was purified by flash chromatography (5% EtOAc-hexane) to provide the title compound.

Workup

temperatureThe reaction was warmed to RT
concentrationThe mixture was concentrated in vacuo
dissolutionThe residue was dissolved in EtOAc (400 mL)
washwashed with saturated NH4Cl (twice), water, and brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe crude was purified by flash chromatography (5% EtOAc-hexane)

Sources & evidence

ORD record: ord-b510c81b584a457e9b0d976ede1b5800
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199244B2

Reaction notes

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