Methanol → Diethyl-3-aminoadipate

HRID 2225970Notes

Reaction equation

HRID 2225970 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-aminoadipateYield 75%

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 was 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-aminoadipate (7.5 g). 1H NMR (d6-DMSO) δ 1.25 (t, 3H, J=8 Hz), 1.26 (t, 3H, J=8 Hz), 1.8 (m,2H), 1.55 (bs, 2H), 3.18 (m, 1H), 4.13 (q, 4H, J=8 Hz), 4.15 (q, 4H, J=8 Hz); MS (FAB) m/z 218.3 (MH+).

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. extractionwas extracted with ether (100 ml)
  7. extractionThe product was extracted into methylene chloride
  8. dry with materialdried over Na2SO4
  9. customevaporated

Sources & evidence

ORD record
ord-3cbc10aee4274569ba2eb2a1facc4711
Source dataset
uspto-grants-1994_09
Patent number
US05344957

Reaction notes

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