(1R*,2R*,5S*,6R*)-8-benzyl-2-(3-hydroxypropynyl)-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]octan-2-ol → (1R*,2R*,5S*,6R*)-8-Benzyl-2-[(Z)-3-hydroxypropenyl]-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]octan-2-ol

HRID 1017265Notes

Reaction equation

HRID 1017265 reaction equation
[CH2:1]([N:8]1[C@@H:13]2[C@H:14]([S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH2:15][C@@:9]1([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C@@:10]([C:26]#[C:27][CH2:28][OH:29])([OH:25])[CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].C(OCC)(=O)C>[CH2:1]([N:8]1[C@@H:13]2[C@H:14]([S:16]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)(=[O:17])=[O:18])[CH2:15][C@@:9]1([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C@@:10](/[CH:26]=[CH:27]\[CH2:28][OH:29])([OH:25])[CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 70152384(1R*,2R*,5S*,6R*)-8-benzyl-2-(3-hydroxypropynyl)-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]octan-2-ol

Product 1

HCID 70151880(1R*,2R*,5S*,6R*)-8-Benzyl-2-[(Z)-3-hydroxypropenyl]-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]octan-2-olYield 90%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Lindlar catalyst (200 mg) was added to a solution of (1R*,2R*,5S*,6R*)-8-benzyl-2-(3-hydroxypropynyl)-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]octan-2-ol (Description 13; 2.1 g, 4.3 mmol) in ethyl acetate (100 ml). The mixture was stirred at room temperature for 8 hours then filtered through Celite™ and the filtrate concentrated in vacuo to yield the title compound (1.88 g, 90%).

Workup

  1. filtrationthen filtered through Celite™
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-5122bfc9173b492a96e6230ea6007a67
Source dataset
uspto-grants-2002_11
Patent number
US06479486B2

Reaction notes

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