Sulfuric Acid → HCID 86702283, compound
Reaction equation
[CH2:1]([N:8]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:9]([C@@H:11]1[CH2:16][CH2:15][C:14](=[N:17][O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:13][NH:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[BH4-].[Na+].[OH-].[Na+]>O.C(OCC)(=O)C.C(#N)C.O1CCCC1>[CH2:26]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]([C@@H:11]1[CH2:16][CH2:15][C@@H:14]([NH:17][O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:13][NH:12]1)=[O:10])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- -10 °C
Procedure
Under nitrogen atmosphere, tetrahydrofuran (1.6 ml) and acetonitrile (0.4 ml) were added to (2S)-5-benzyloxyimino-piperidine-2-carboxylic acid dibenzylamide (0.214 g, 0.50 mmol), and the obtained mixture was cooled down to −10° C. Sulfuric acid (0.302 g, 3.06 mmol) was added to the mixture, and then sodium borohydride (0.0757 g, 2.00 mmol) was added. After 22 hours of stirring, ethyl acetate (10 ml) and water (5 ml) were added to the mixture, the pH of the mixture was adjusted at 11 with 30% by weight sodium hydroxide aqueous solution, and the obtained mixture was separated. The organic layer was dried with anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 0.176 g of the title compound (yield: 82%). The diastereo selectivity was (2S,5R)/(2S,5S)=87.7/12.3 (75.4% de).
Workup
- customthe obtained mixture was separated
- dry with materialThe organic layer was dried with anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-df7087f7730940c98e2c3cda297f087a
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096523B2
Reaction notes
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