Methanesulfonic Acid → 5-(N,N-Diethylaminomethyl)-3-(2,5-dimethoxybenzylamino)-2-diphenylmethyl-1-azabicyclo[2.2.2]octane

HRID 1458892

반응식

HRID 1458892 반응식
[CH2:1]([N:3]([CH2:39][CH3:40])[C:4]([CH:6]1[CH:11]2[CH2:12][CH2:13][N:8]([CH:9]([CH:26]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:10]2[NH:14][CH2:15][C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=2[O:24][CH3:25])[CH2:7]1)=O)[CH3:2].[O-]S([O-])(=O)=O.[Na+].[Na+].CS(O)(=O)=O>C1COCC1.CC(C)=O>[CH2:39]([N:3]([CH2:4][CH:6]1[CH2:7][N:8]2[CH2:13][CH2:12][CH:11]1[CH:10]([NH:14][CH2:15][C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=1[O:24][CH3:25])[CH:9]2[CH:26]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:1][CH3:2])[CH3:40]

참가 물질

6

반응물 3

HCID 6395Methanesulfonic AcidHCID 24436Sodium SulfateHCID 10165826N,N-Diethyl-5-(2,5-dimethoxy benzylamino)-6-diphenylmethyl-1-azabicyclo[2.2.2]octane-3-carboxamide

생성물 1

HCID 701157215-(N,N-Diethylaminomethyl)-3-(2,5-dimethoxybenzylamino)-2-diphenylmethyl-1-azabicyclo[2.2.2]octane수율 57%

시약·촉매·용매 2

HCID 180Acetone용매HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 19 (300 mg, 0.55 mmole) in dry THF (2 ml) was added to a suspension of LiAIH4 (105 mg, 2.75 mmole) in 5 ml of dry THF at 5° C. and stirred at room temperature for 1 hour. Na2SO4 /10H2O (2 g) was added to the reaction mixture and stirred for 15 hours at room temperature. The suspension was filtrated, and the solids were washed with dry THF. The filtrate was concentrated under reduced pressure. The resulting oil was dissolved in 2 ml of acetone, and CH3SO3H (159 mg, 1.65 mmole) was added to the solution of the crude oil in acetone (2 ml). The resulting precipitate was collected by filtration and dried in vacuo to give 20 (254 mg, 0.31 mmole, 57%).

후처리

  1. stirringstirred for 15 hours at room temperature
  2. filtrationThe suspension was filtrated
  3. washthe solids were washed with dry THF
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. dissolutionThe resulting oil was dissolved in 2 ml of acetone
  6. filtrationThe resulting precipitate was collected by filtration
  7. customdried in vacuo

출처 및 근거

ORD 기록
ord-fdc3a328f762429494463eeedb04a933
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05852038

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