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

Reaktionsgleichung

Reaktionsgleichung von HRID 862120
[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]

Komponenten

8

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c376f54116164601bb3cb227d3bc7c41
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05716965

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