Methanol → Dimethyl 3-aminopentanedioate

HRID 1941545Notes

Reaction equation

HRID 1941545 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5](=O)[CH2:6][C:7]([O:9][CH3:10])=[O:8].CO.C([O-])=O.[NH4+].[BH3-]C#[N:21].[Na+]>Cl>[CH3:1][O:2][C:3](=[O:12])[CH2:4][CH:5]([NH2:21])[CH2:6][C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 4

HCID 887MethanolHCID 74591Dimethyl 3-oxoglutarateHCID 2723923Ammonium formateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 253304Dimethyl 3-aminopentanedioateYield 75.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Dimethyl-3-oxoglutarate (10 g, 57 mmol) was added to methanol (225 ml) followed by ammonium formate (36 g, 570 mmol) and NaBH3CN (3.7 g, 57 mmol) at 25° C. After 24 h, the methanol was removed in white mass. Methylene chloride was added and the mixture filtered. The methylene chloride was evaporated resulting in an oil which was dissolved in 1N HCl (200 ml) and extracted with ether (100 ml). The ether layer was discarded and the aqueous layer was made basic using solid K2CO3. The product was extracted into methylene chloride, dried over Na2 SO4, and evaporated to give dimethyl-3-aminoglutarate (7.5 g). 1H NMR (d6-DMSO) δ1.76 (bs, 2H), 2.45 (dd, 4H, J=8.1 Hz, 16.6 Hz), 3.69 (s, 6H), 5.45 (m, 1H); MS (FAB) m/z 176.0 (MH+).

Workup

  1. customthe methanol was removed in white mass
  2. additionMethylene chloride was added
  3. filtrationthe mixture filtered
  4. customThe methylene chloride was evaporated
  5. customresulting in an oil which
  6. extractionextracted with ether (100 ml)
  7. extractionThe product was extracted into methylene chloride
  8. customdried over Na2 SO4
  9. customevaporated

Sources & evidence

ORD record
ord-416dca125cd244f4942c475cba783653
Source dataset
uspto-grants-1997_12
Patent number
US05703125

Reaction notes

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