Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → (2S,5R)-benzyl 5-(benzyloxyamino)piperidine-2-carboxylate
Reaction equation
C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.[CH2:16]([O:23][C:24]([C@@H:26]1[CH2:31][CH2:30][C:29](=[N:32][O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:28][NH:27]1)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.B.O1CCCC1>O1CCCC1>[CH2:16]([O:23][C:24]([C@@H:26]1[CH2:31][CH2:30][C@@H:29]([NH:32][O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:28][NH:27]1)=[O:25])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
Under nitrogen atmosphere, (±)-camphorsulfonic acid (0.697 g, 3.00 mmol) and tetrahydrofuran (2 ml) was added to (2S)-5-benzyloxyimino-piperidine-2-carboxylic acid benzyl ester (0.169 g, 0.50 mmol), and the mixture was cooled down to −20° C. Borane-tetrahydrofuran complex (1.06 M tetrahydrofuran solution, 2.4 ml, 2.54 mmol) was added to the mixture for 1.5 hours, and the obtained mixture was stirred for 6 hours. The reaction mixture was analyzed with high performance liquid chromatography to find that the reaction mixture contained 0.140 g of the title compound, and the reduction reaction proceeded with yield of 82%. The diastereo selectivity was (2S,5R)/(2S,5S)=87.8/12.2 (75.6% de).
Sources & evidence
- ORD record
- ord-06368c262d864600b0d9fc8a31bcdfaa
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096523B2
Reaction notes
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