3-Pyridinecarboxaldehyde → 5-Oxo-1-(3-pyridinylmethyl)proline

HRID 554140

반응식

HRID 554140 반응식
[NH2:1][C@@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5]([OH:7])=O.[OH-].[Na+].[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]=O)[CH:14]=1.[BH4-].[Na+]>C(O)C>[O:7]=[C:5]1[N:1]([CH2:19][C:15]2[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=2)[C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4]1

참가 물질

6

반응물 4

HCID 103713-PyridinecarboxaldehydeHCID 14798Sodium HydroxideHCID 23327D-Glutamic AcidHCID 4311764Sodium borohydride

생성물 1

HCID 105368875-Oxo-1-(3-pyridinylmethyl)proline수율 61.8%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

D-glutamic acid (2.21 g, 15 mmol) was dissolved in 2N aqueous sodium hydroxide (15 ml, 30 mmol) at 0° C. and then treated with pyridine-3-carboxaldehyde (1.41 ml, 15 mmol) in ethanol (3 ml). The mixture was stirred at room temperature for 30 minutes and then cooled to 0° C. and treated portion-wise with sodium borohydride (0.189 g, 5 mmol). The mixture was allowed to warm to room temperature with stirring over 4 hrs then after washing with diethyl ether it was acidified to pH5-6 using concentrated hydrochloric acid. The resulting precipitate was collected by filtration, washed with diethyl ether, and dried in vacuo. This material was then taken up in ethanol (50 ml) and refluxed overnight. Fine solids were removed by filtration and then concentration gave 5-oxo-1-(3-pyridinylmethyl)proline (2.04 g) as a white solid which was used without any further purification.

후처리

  1. temperaturecooled to 0° C.
  2. temperatureto warm to room temperature
  3. stirringwith stirring over 4 hrs
  4. washafter washing with diethyl ether it
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with diethyl ether
  7. customdried in vacuo
  8. temperaturerefluxed overnight
  9. customFine solids were removed by filtration
  10. concentrationconcentration

출처 및 근거

ORD 기록
ord-753fcc2df7464fd19953f6b1a095e7f5
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08048907B2

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