Mesoxalic acid → 8-Benzyl-8-azabicyclo(3.2.1)octan-3-one

HRID 433117

반응식

HRID 433117 반응식
CO[CH:3]1[CH2:7][CH2:6][CH:5](OC)[O:4]1.Cl.[CH2:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O=[C:20]([C:24](O)=O)[C:21](O)=O.C([O-])(=O)C.[Na+].[OH-].[Na+]>Cl>[CH2:11]([N:18]1[CH:6]2[CH2:5][CH2:24][CH:20]1[CH2:21][C:3](=[O:4])[CH2:7]2)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

7

반응물 5

HCID 10132Mesoxalic acidHCID 14798Sodium HydroxideHCID 790982,5-DimethoxytetrahydrofuranHCID 517045Sodium AcetateHCID 2724127Benzylammonium chloride

생성물 1

HCID 1198468-Benzyl-8-azabicyclo(3.2.1)octan-3-one

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

반응 조건

온도
50 °C

실험 절차

A solution of 2,5-dimethoxytetrahydrofuran (50 g, 378 mmol) in 0.025 M aqueous hydrochloric acid (160 ml) was cooled to 0° C. and stirred for 16 hours. Benzylamine hydrochloride (65 g, 453 mmol), ketomalonic acid (55 g, 377 mmol) and an aqueous solution of sodium acetate (300 ml, 0.69 M) were added and the reaction stirred at room temperature for 1 hour. The mixture was heated to 50° C. for a further 90 minutes then cooled in an ice bath and basified to pH12 with 2 N aqueous sodium hydroxide solution. The layers were separated, and the aqueous phase extracted with ethyl acetate (3×). The combined organic solutions were washed with water, dried (MgSO4), filtered and evaporated under reduced pressure. The residual brown oil was distilled under reduced pressure (126° C./0.4 kPa) to afford the title compound as an off-white solid, 37.81 g.

후처리

  1. stirringthe reaction stirred at room temperature for 1 hour
  2. temperaturethen cooled in an ice bath
  3. customThe layers were separated
  4. extractionthe aqueous phase extracted with ethyl acetate (3×)
  5. washThe combined organic solutions were washed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. distillationThe residual brown oil was distilled under reduced pressure (126° C./0.4 kPa)

출처 및 근거

ORD 기록
ord-a96b865394804e97888a20ceefdfd451
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06667314B2

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