Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → (3R*,4S*,5S*,6S*)-N,N-Diethyl-5-(2,5-dimethoxybenzylamino)-6-diphenylmethyl-1-azabicyclo[2.2.2]octane-3-carboxamide

HRID 862120

반응식

HRID 862120 반응식
[CH2:1]([N:3]([CH2:28][CH3:29])[C:4]([C@@H:6]1[C@@H:11]2[CH2:12][CH2:13][N:8]([CH:9]([CH:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:10]2=O)[CH2:7]1)=[O:5])[CH3:2].[CH3:30][O:31][C:32]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][C:33]=1[CH2:34][NH2:35].C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1(C)C=CC=CC=1.C(O)(=O)C.O>[CH2:1]([N:3]([CH2:28][CH3:29])[C:4]([C@@H:6]1[C@@H:11]2[CH2:12][CH2:13][N:8]([C@@H:9]([CH:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C@H:10]2[NH:35][CH2:34][C:33]2[CH:36]=[C:37]([O:40][CH3:41])[CH:38]=[CH:39][C:32]=2[O:31][CH3:30])[CH2:7]1)=[O:5])[CH3:2]

참가 물질

8

반응물 4

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 186522,5-DimethoxybenzenemethanamineHCID 5049666Sodium triacetoxyborohydrideHCID 53867570(3R*,4S*)-N,N-Diethyl-6-diphenylmethyl-5-oxo-1-azabicyclo[2.2.2]octane-3-carboxamide

생성물 1

HCID 57263206(3R*,4S*,5S*,6S*)-N,N-Diethyl-5-(2,5-dimethoxybenzylamino)-6-diphenylmethyl-1-azabicyclo[2.2.2]octane-3-carboxamide수율 44%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매HCID 1140Toluene용매

실험 절차

A mixture of 23 (3.9 g, 10 mmol), 2,5-dimethoxybenzyl amine (1.9 g, 11 mmol) (Acta. Chem. Scand., 25. p. 2629 (1971)) and camphor sulfonic acid (120 mg) in toluene (40 ml) was heated at reflux with removal of water for 8 hours and then the solvent was removed. The residue was dissolved in small amount of THF (c.a. 5 ml) and this solution was added to a solution of sodium triacetoxyborohydride (5.3 g, 25 mmol) in acetic acid (100 ml) at room temperature. The mixture was stirred at room temperature for 4 hours and the solvent was removed. Water (25 ml) was added and the mixture was neutralized with NaHCO3 and extracted with EtOAc three times. The clude was purified by recrystallization from EtOAc to give 24 (2.4 g, 4.4 mmol, 44%).

후처리

  1. temperaturewas heated
  2. customthe solvent was removed
  3. dissolutionThe residue was dissolved in small amount of THF (c.a. 5 ml)
  4. customthe solvent was removed
  5. additionWater (25 ml) was added
  6. extractionextracted with EtOAc three times
  7. customThe clude was purified by recrystallization from EtOAc

출처 및 근거

ORD 기록
ord-c376f54116164601bb3cb227d3bc7c41
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05716965

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