Methanol → HCID 21834683, compound

HRID 1741192Notes

Reaction equation

HRID 1741192 reaction equation
[C:1]([CH:4]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[C:5]([O:7][CH3:8])=[O:6])(=O)[CH3:2].CO.C([O-])=O.[NH4+].[BH3-]C#[N:22].[Na+]>Cl.C(Cl)Cl>[CH3:8][O:7][C:5](=[O:6])[CH:4]([CH2:1][CH2:2][NH2:22])[CH2:9][C:10]([O:12][CH3:13])=[O:11]

Participants

7

Reactant 4

HCID 887MethanolHCID 112039Dimethyl acetylsuccinateHCID 2723923Ammonium formateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 21834683HCID 21834683, compoundYield 59.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

Dimethyl acetylsuccinate (10 g, 53 mmol) was added to methanol (200 ml) followed by ammonium formate (34 g, 530 mmol) and NaBH3CN (3.4 g, 53 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 dimethyl-2-(aminoethyl)succinate (6 g). 1H NMR (d6-DMSO) δ 0.97 (d, 3H, J=7.1 Hz), 2.66 (m, 2H), 3.05 (m, 1H), 3.56 (s, 3H), 3.60 (s, 3H), 4.15 (m, 1H); MS (FAB) m/z 190.2 (MH+), 158.2, 141.2.

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

Sources & evidence

ORD record
ord-4d5e456841594fdcac573eea1a32f5b6
Source dataset
uspto-grants-1999_10
Patent number
US05973003

Reaction notes

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