Methanol → Diethyl-3-aminoadipate

HRID 2255296ノート

反応式

HRID 2255296 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 21834720Diethyl-3-aminoadipate

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 6344Dichloromethane溶媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-d3593cb98ccd4df7a6fff396a862536f
出典データセット
uspto-grants-1993_08
特許番号
US05239113

反応ノート

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