tert-butyl 8,8-dimethyl-6-oxo-3,4,7,8-tetrahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline-2(6H)-carboxylate → tert-butyl 8,8-dimethyl-3,4,7,8-tetrahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline-2(6H)-carboxylate
Reaction equation
[CH3:1][C:2]1([CH3:24])[C:11]2[C:6]3=[C:7]([CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15][N:5]3[C:4](=O)[CH2:3]1)[CH:8]=[CH:9][CH:10]=2>O1CCCC1>[CH3:1][C:2]1([CH3:24])[C:11]2[C:6]3=[C:7]([CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15][N:5]3[CH2:4][CH2:3]1)[CH:8]=[CH:9][CH:10]=2Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 38 mg (0.115 mmol) tert-butyl 8,8-dimethyl-6-oxo-3,4,7,8-tetrahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline-2(6H)-carboxylate of step 1.2 in 1 mL of tetrahydrofuran was treated with 0.46 mL of 1 molar solution of borohydride-tetrahydrofuran complex in tetrahydrofuran. The mixture was stirred over night, and then quenched with water and diluted hydrochloric acid. The pH was adjusted to pH 9 by addition of aqueous sodium hydroxide solution and the mixture extracted three times with 10 mL of dichloromethane each. The solution was dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica (eluent: 20-30% ethyl acetate in heptane) to yield 21 mg of the title compound as a clear oil.
Workup
- customquenched with water and diluted hydrochloric acid
- additionThe pH was adjusted to pH 9 by addition of aqueous sodium hydroxide solution
- extractionthe mixture extracted three times with 10 mL of dichloromethane each
- dry with materialThe solution was dried over magnesium sulfate
- concentrationconcentrated in vacuo
- customThe residue was purified by column chromatography on silica (eluent: 20-30% ethyl acetate in heptane)
Sources & evidence
- ORD record
- ord-c7962a30f577445c9ccfe80f48c87def
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09169253B2
Reaction notes
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