Water → Dimethyl 3-aminopentanedioate

HRID 378132

Reaction equation

HRID 378132 reaction equation
O=[C:2]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH2:3][C:4]([O:6][CH3:7])=[O:5].C([O-])=O.[NH4+].[BH3-]C#[N:19].[Na+].O>CO>[NH2:19][CH:2]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH2:3][C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 74591Dimethyl 3-oxoglutarateHCID 2723923Ammonium formateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 253304Dimethyl 3-aminopentanedioateYield 44.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dimethyl 3-ketoglutarate (13 g) in methanol (50 ml) was treated with ammonium formate (5 g) and NaCNBH3 (2 g). 10 ml of H2O was added and the excess solvent removed under reduced pressure. The semi-solid was dissolved in 5% aqueous HCl (250 ml), and washed with CH2Cl2 (2×50 ml). The aqueous layer was made basic (pH>9) with K2CO3 and the product was extracted using CH2Cl2 (2×75 ml). The organic layers were combined and dried with Na2SO4. The excess solvent was removed to give 2.5 g of the dimethyl (±)3-aminoglutarate. This was dissolved in methanol (50 ml) and treated with 4N HCl/Dioxane (10 ml). The excess solvent was removed under reduced pressure to give a 2.7 g of dimethyl (±)3-aminoglutarate hydrochloride. MS and 1H-NMR were consistent with the desired product.

Workup

  1. customthe excess solvent removed under reduced pressure
  2. dissolutionThe semi-solid was dissolved in 5% aqueous HCl (250 ml)
  3. washwashed with CH2Cl2 (2×50 ml)
  4. extractionthe product was extracted
  5. dry with materialdried with Na2SO4
  6. customThe excess solvent was removed

Sources & evidence

ORD record
ord-75cca8b566924213a2028830e6c65034
Source dataset
uspto-grants-2000_02
Patent number
US06028223

Linked notes

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