Diethyl Ether → 3-[4-(10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-10-carbonyl)-phenyl]-2-methyl-cyclohex-2-en-1-one
Reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15]([C:17]3[CH:22]=[CH:21][C:20](B4OC(C)(C)C(C)(C)O4)=[CH:19][CH:18]=3)=[O:16])[CH2:6][C:5]=12.C([O:34][CH2:35][CH3:36])C>>[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15]([C:17]3[CH:18]=[CH:19][C:20]([C:1]4[CH2:2][CH2:3][CH2:36][C:35](=[O:34])[C:5]=4[CH3:6])=[CH:21][CH:22]=3)=[O:16])[CH2:6][C:5]=12Participants
3
Procedure
(10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone of Example 19, Step B (0.350 g, 0.87 mmol) and 3-oxo-2-methyl-cylclohex-1-en-1-yl trifluoromethanesulfonate (0.248 g, 0.96 mmol) were reacted in the manner of Example 1, Step F. Purification by flash column chromatography on silica gel, eluting with a solvent gradient of from 20 to 50% ethyl acetate in hexane afforded a light yellow oil. The oil thus isolated was dissolved in boiling diethyl ether and precipitated by addition of petroleum ether. The precipitate was filtered and dried to afford the title compound (0.297 g) as a white solid, m.p. 95–97° C.
Workup
- customPurification by flash column chromatography on silica gel
- washeluting with a solvent gradient of from 20 to 50% ethyl acetate in hexane
- customafforded a light yellow oil
- customThe oil thus isolated
- dissolutionwas dissolved
- customprecipitated by addition of petroleum ether
- filtrationThe precipitate was filtered
- customdried
Sources & evidence
- ORD record
- ord-180f57f544f643f2bf6e0d1983c29f15
- Source dataset
- uspto-grants-2006_04
- Patent number
- US07022699B2
Reaction notes
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