Methanol → Diethyl-3-aminoadipate

HRID 2255296Notes

Reaction equation

HRID 2255296 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6](=O)[CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH3:2].CO.C([O-])=O.[NH4+].[BH3-]C#[N:24].[Na+]>Cl.C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][CH:6]([NH2:24])[CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH3:2]

Participants

7

Reactant 4

HCID 887MethanolHCID 81576Diethyl 3-oxoadipateHCID 2723923Ammonium formateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 21834720Diethyl-3-aminoadipate

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

Diethyl-3-oxoadipate (10 g, 46 mmol) was added to methanol (225 ml) followed by ammonium formate (27.4 g, 460 mmol) and NaBH3CN (2.7 g, 46 mmol) at 25° C. After 24 h the methanol was removed in vacuo to leave a 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 Na2SO4 and evaporated to give Diethyl-3-aminopimaleate (7.5 g). 1H NMR (d6-DMSO) δ 1.25 (t, 3H, J=8Hz), 1.26 (t, 3H, J=8Hz), 1.8 (m,2H), 1.55 (bs, 2H), 3.18 (m, 1H), 4.13 (q, 4H, J=8Hz), 4.15 (q, 4H, J=8Hz); MS (FAB) m/e 218.3 (M+H+).

Workup

  1. customAfter 24 h the methanol was removed in vacuo
  2. customto leave a white mass
  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. dry with materialdried over Na2SO4
  9. customevaporated
  10. customto give Diethyl-3-aminopimaleate (7.5 g)

Sources & evidence

ORD record
ord-d3593cb98ccd4df7a6fff396a862536f
Source dataset
uspto-grants-1993_08
Patent number
US05239113

Reaction notes

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