Disodium 2,3-dihydroxybutanedioate → Benzyl 4-formylpiperidine-1-carboxylate

HRID 2252047Notes

Reaction equation

HRID 2252047 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH2:11]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24]([C:27](OCC)=[O:28])[CH2:23][CH2:22]1)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])(=O)C(C(C([O-])=O)O)O.[Na+].[Na+]>ClCCl>[CH2:11]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24]([CH:27]=[O:28])[CH2:23][CH2:22]1)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 13355Disodium 2,3-dihydroxybutanedioateHCID 152896721-Benzyl 4-ethyl piperidine-1,4-dicarboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 2776272Benzyl 4-formylpiperidine-1-carboxylateYield 53.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Add diisobutyl aluminum hydride (1 M in toluene, 30 mL, 30 mmol) over 5 minutes to a solution of 1-(benzyloxycarbonyl)-4-(ethoxycarbonyl)piperidine (7 g, 24 mmol) in anhydrous dichloromethane (150 mL) at −78° C. under a nitrogen atmosphere. Stir the reaction mixture at this temperature for 30 minutes and then add 10% aqueous sodium tartarate (100 mL) followed by dichloromethane. Stir the reaction mixture at room temperature overnight. Separate the phases and extract the aqueous phase with dichloromethane. Wash the combined organic phases sequentially with 10% aqueous sodium tartarate, water, and saturated aqueous sodium chloride. Dry over sodium sulfate and concentrate under reduced pressure. Subject the residue to silica gel chromatography, eluting with 3:1 hexanes:ethyl acetate to provide 3.15 g (53%) of the title compound.

Workup

  1. stirringStir the reaction mixture at room temperature overnight
  2. customSeparate the phases
  3. extractionextract the aqueous phase with dichloromethane
  4. washWash the combined organic phases sequentially with 10% aqueous sodium tartarate, water, and saturated aqueous sodium chloride
  5. dry with materialDry over sodium sulfate
  6. concentrationconcentrate under reduced pressure
  7. washeluting with 3:1 hexanes

Sources & evidence

ORD record
ord-14f61a6300a04035a5a89cd122822e46
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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