Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Bisulfate | HCID 516919 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | Calcium Chloride | HCID 5284359 | — |
| Reactant | HCID 59625536 | HCID 59625536 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 58355453 | HCID 58355453 | 93.9% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09221836B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-18fea07fcdd940cd9ee7d49153f6efab |
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| Source note | uspto-grants-2015_12 |
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