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

HRID 1017275Notes

Reaction equation

HRID 1017275 reaction equation
[CH2:1]([N:8]1[C@@H:13]2[CH:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][C@@:9]1([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C@:10]([C:24]#[C:25][CH2:26][OH:27])([OH:23])[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[CH:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][C@@:9]1([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C@:10](/[CH:24]=[CH:25]\[CH2:26][OH:27])([OH:23])[CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 70152056(1R*,2S*,5S*,6RS)-8-Benzyl-6-(tert-butoxycarbonyl)-2-(3-hydroxypropynyl)-1-phenyl-8-azabicyclo[3.2.1]octan-2-ol

Product 1

HCID 70153639(1R*,2S*,5S*,6RS)-8-Benzyl-6-(tert-butoxycarbonyl)-2-[(Z)-3-hydroxypropenyl]-1-phenyl-8-azabicyclo[3.2.1]octan-2-olYield 100%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (1R*,2S*,5S*,6RS)-8-benzyl-2-(3-hydroxypropynyl)-1-phenyl-6-(tert-butoxycarbonyl)-8-azabicylco[3.2.1]octan-2-ol (Description 25; a 3:1 mixture of C6 epimers, 4 g, 8.9 mmol), Lindlar catalyst (800 mg) and ethyl acetate (30 ml) was stirred under hydrogen atmosphere (1 atm) at room temperature for 45 minutes. The reaction mixture was filtered through a pad of Celite™. The filtrate was concentrated to give the title compound (4.0 g, 100%) as a 3:1 mixture of C6 epimers.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite™
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-7a692c6b07434a5b8eefd8db8378e646
Source dataset
uspto-grants-2002_11
Patent number
US06479486B2

Reaction notes

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