Sodium Sulfate → (2R*,3R*,4R*,5R*)-5-(N,N-Diethylaminomethyl)-3-(2,5-dimethoxybenzylamino)-2-diphenylmethyl-1-azabicyclo[2.2.2]octane

HRID 862121Notes

Reaction equation

HRID 862121 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:9]([CH2:45][CH3:46])[C:10]([C@@H:12]1[C@@H:17]2[CH2:18][CH2:19][N:14]([C@@H:15]([CH:32]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C@H:16]2[NH:20][CH2:21][C:22]2[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:23]=2[O:30][CH3:31])[CH2:13]1)=O)[CH3:8].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH2:45]([N:9]([CH2:10][C@@H:12]1[CH2:13][N:14]2[CH2:19][CH2:18][C@H:17]1[C@@H:16]([NH:20][CH2:21][C:22]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:23]=1[O:30][CH3:31])[C@H:15]2[CH:32]([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH2:7][CH3:8])[CH3:46]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 57263206(3R*,4S*,5S*,6S*)-N,N-Diethyl-5-(2,5-dimethoxybenzylamino)-6-diphenylmethyl-1-azabicyclo[2.2.2]octane-3-carboxamide

Product 1

HCID 70116643(2R*,3R*,4R*,5R*)-5-(N,N-Diethylaminomethyl)-3-(2,5-dimethoxybenzylamino)-2-diphenylmethyl-1-azabicyclo[2.2.2]octaneYield 95.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of lithium aluminum hydride (80 mg, 2.1 mmol) in THF (10 ml) was added 24 (220 mg, 0.41 mmol) at room temperature. The mixture was stirred at room temperature for 2 hours. Na2SO4 /10H2O (320 mg, 1 mmol) was added then the mixture was stirred for 10 minutes. After removal of the precipitate, the solution was concentrated. The residue was dissolved in hexane (20 ml) then filtered and concentrated to give 25 (210 mg, 0.39 mmol, 95%) as a colorless oil.

Workup

  1. stirringthe mixture was stirred for 10 minutes
  2. customAfter removal of the precipitate
  3. concentrationthe solution was concentrated
  4. dissolutionThe residue was dissolved in hexane (20 ml)
  5. filtrationthen filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7d4e3313b75f408e980d079c584a77c8
Source dataset
uspto-grants-1998_02
Patent number
US05716965

Reaction notes

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