Borane → HCID 15516069, compound
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]([CH:23]1[CH2:32][CH2:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24]1)=O)(=[O:12])=[O:11])([O-])=O.B>O1CCCC1>[CH2:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:31][CH2:32][CH:23]1[CH2:21][NH:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][NH:13][S:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[NH2:1])(=[O:12])=[O:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1,2,3,4-tetrahydro-2-naphthalencarboxylic acid[6-(2-nitrobenzenesulfonylamino)-hexyl]-amide (0.090 g, 0.19 mmol) in tetrahydrofuran (5 mL) cooled to 0° C. was added 2 mL 1M solution of borane:THF complex and the reaction mixture was refluxed for 12 h. The reaction mixture was cooled in an ice bath and quenched with 2 mL of 1N HCl. The reaction mixture was neutralized with 10% aqueous sodium hydroxide solution and extracted with ethyl acetate (3×25 mL). The organic phase was washed with brine, dried over sodium sulfate, and evaporated in vacuo to afford an oil which was purified by preparative TLC to afford the titled compound (0.06 g, 70%); hydrochloride salt mp (162-163° C.).
Workup
- temperatureTHF complex and the reaction mixture was refluxed for 12 h
- temperatureThe reaction mixture was cooled in an ice bath
- customquenched with 2 mL of 1N HCl
- extractionextracted with ethyl acetate (3×25 mL)
- washThe organic phase was washed with brine
- dry with materialdried over sodium sulfate
- customevaporated in vacuo
- customto afford an oil which
- customwas purified by preparative TLC
Sources & evidence
- ORD record
- ord-318b2fe42a424afa990edabed4771b5b
- Source dataset
- uspto-grants-2001_04
- Patent number
- US06211241B1
Reaction notes
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