Citric Acid → HCID 59625498, compound

HRID 2192808Notes

Reaction equation

HRID 2192808 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH2:29][CH:30]([CH3:32])[CH3:31])[CH:12]1[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:15][CH:14]([C:25](OC)=[O:26])[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Ca+2].[Cl-].[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.C(O)C>[CH2:1]([O:8][C:9]([N:11]([CH2:29][CH:30]([CH3:32])[CH3:31])[CH:12]1[CH2:13][CH:14]([CH2:25][OH:26])[CH2:15][N:16]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:17]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 59625482HCID 59625482, compound

Product 1

HCID 59625498HCID 59625498, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-tert-butyl 3-methyl 5-{[(benzyloxy)carbonyl](2-methylpropyl)amino}piperidine-1,3-dicarboxylate (13.0 g) in THF (100 ml) was added to a solution of calcium chloride (6.5 g) and sodium borohydride (4.5 g) in ethanol (100 ml) under ice-cooling, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was adjusted to pH 4 with 10% aqueous citric acid solution, and concentrated under reduced pressure to a half volume. The residue 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. The residue was subjected to silica gel column chromatography, and the fraction eluted with ethyl acetate-hexane (5:95-80:20) was concentrated under reduced pressure to give the object compound (8.04 g).

Workup

  1. temperaturecooling
  2. concentrationconcentrated under reduced pressure to a half volume
  3. extractionThe residue was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. washthe fraction eluted with ethyl acetate-hexane (5:95-80:20)
  8. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-307dfda2d7c9418a8e38fe3124f40d5a
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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