Sodium Bisulfate → HCID 58355453, compound
Reaction equation
[Cl-].[Ca+2].[Cl-].[BH4-].[Na+].[CH2:6]([O:13][C:14]([N:16]([CH2:34][CH:35]([CH3:37])[CH3:36])[C@@H:17]1[CH2:22][N:21]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:20][C@H:19]([C:30](OC)=[O:31])[CH2:18]1)=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.S([O-])(O)(=O)=O.[Na+]>C(O)C.C1COCC1>[CH2:6]([O:13][C:14]([N:16]([CH2:34][CH:35]([CH3:37])[CH3:36])[C@H:17]1[CH2:18][C@@H:19]([CH2:30][OH:31])[CH2:20][N:21]([C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[CH2:22]1)=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1Participants
7
Conditions
- Temperature
- 0 °C
Procedure
Powder calcium chloride (0.49 g) was suspended in ethanol (10 ml), sodium borohydride (0.34 g) was added while cooling to 0° C., and the mixture was stirred at 0° C. for 30 min. A solution (10 ml) of 1-tert-butyl 3-methyl (3R,5S)-5-{[(benzyloxy)carbonyl](2-methylpropyl)amino}piperidine-1,3-dicarboxylate (1.00 g) in THF was added to the reaction suspension, and the mixture was stirred at 0° C. for 8 hr. 5% Aqueous sodium hydrogen sulfate solution was added to the reaction mixture for neutralization and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the object product (0.88 g) as an oil.
Workup
- stirringthe mixture was stirred at 0° C. for 8 hr
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-616c54b126ea46aca0113e1f903dfacb
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08664380B2
Reaction notes
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