1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 10448426, compound

HRID 1080895Notes

Reaction equation

[Si:1]([O:8][CH2:9][C:10]1[S:11][S:12][C:13]([CH2:16]O)=[CH:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1(P([N:32]=[N+:33]=[N-:34])(C2C=CC=CC=2)=O)C=CC=CC=1.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1>[N:32]([CH2:16][C:13]1[S:12][S:11][C:10]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[CH:15][CH:14]=1)=[N+:33]=[N-:34]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 3.4 g (11.7 mmol) of 3-[(tert-butyldimethylsilyloxy)methyl]-6-hydroxymethyl-1,2-dithiin (10) in 12 mL of toluene was added diphenylphosphoryl azide (3.02 mL; 3.86 g, 14.0 mmol) in 8 mL of toluene and the solution was cooled to 0° C. To the cold solution was added dropwise 2.09 mL (2.13 g; 14.0 mmol) of DBU. The reaction mixture became dark. In 2 hours at 0° C., the reaction mixture was allowed to warm up to room temperature. After 14 hours the reaction mixture was purified on a silica gel column using 5% ethyl acetate in hexane to give 2.75 g (74.5%) of azide 15. 1H NMR (CDCl3) δ6.38 (m, 2H, C=CH), 4.30 (s, 2H, CH2O), 3.98 (s, 2H, CH2O), 0.92 (s, 9H, CCH3), 0.10 (s, 6H, SiCH3). 13C NMR (CDCl3) δ136.898 128.007, 123.471, 64.726, 55,145, 25.780, 25.735, 18.278, -5.443; MS (EI) m/z=315.1 (100%; M+).

Workup

temperatureto warm up to room temperature
customAfter 14 hours the reaction mixture was purified on a silica gel column

Sources & evidence

ORD record: ord-410cf26cc3ce4b80a474e7a953ab1631
Source dataset: uspto-grants-1996_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05583235

Reaction notes

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