Methanol → N-(2-nitrobenzenesulfonyl)-N-(2-pyridinylmethyl)-N'-[2-[(t-butyloxycarbonyl)amino]ethyl]-N'-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine
Reaction equation
[C:1](C(N)C=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[N+:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21]([N:24]([CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][N:46]=1)[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][NH:33][CH:34]2[C:43]3[N:42]=[CH:41][CH:40]=[CH:39][C:38]=3[CH2:37][CH2:36][CH2:35]2)=[CH:28][CH:27]=1)(=[O:23])=[O:22])([O-:14])=[O:13].[C:51]([BH3-])#[N:52].[Na+].[CH3:55]O>>[N+:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21]([N:24]([CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][N:46]=1)[CH2:25][C:26]1[CH:27]=[CH:28][C:29]([CH2:32][N:33]([CH2:55][CH2:51][NH:52][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH:34]2[C:43]3[N:42]=[CH:41][CH:40]=[CH:39][C:38]=3[CH2:37][CH2:36][CH2:35]2)=[CH:30][CH:31]=1)(=[O:22])=[O:23])([O-:14])=[O:13]Participants
5
Reactant 4
Product 1
Procedure
Reaction of Boc-aminoacetaldehyde (1.0 mmol) with N-(2-nitrobenzenesulfonyl)-N-(2-pyridinylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (270 mg, 0.5 mmol) in the presence of sodium cyanoborohydride in methanol afforded N-(2-nitrobenzenesulfonyl)-N-(2-pyridinylmethyl)-N′-[2-[(t-butyloxycarbonyl)amino]ethyl]-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (248 mg, 72%). This material was then treated with trifluoroacetic acid (1 mL) in CH2Cl2 (2 mL) for 1 hour. Evaporation of the solvent afforded the primary amine in quantitative yield as the TFA salt.
Sources & evidence
- ORD record
- ord-72fc872b7c744d608edfec602cfa4f88
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07183273B2
Reaction notes
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