tert-Butyl 7-benzyl-9-hydroxy-9-methyl-3,7-diazabicyclo[3.3.1]-nonane-3-carboxylate → Tert-butyl 9-hydroxy-9-methyl-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate

HRID 2180010Notes

Reaction equation

HRID 2180010 reaction equation
C([N:8]1[CH2:15][CH:14]2[C:16]([OH:18])([CH3:17])[CH:10]([CH2:11][N:12]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:13]2)[CH2:9]1)C1C=CC=CC=1>C(O)C.[Pd]>[OH:18][C:16]1([CH3:17])[CH:14]2[CH2:15][NH:8][CH2:9][CH:10]1[CH2:11][N:12]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:13]2

Participants

4

Reactant 1

HCID 22490269tert-Butyl 7-benzyl-9-hydroxy-9-methyl-3,7-diazabicyclo[3.3.1]-nonane-3-carboxylate

Product 1

HCID 22490276Tert-butyl 9-hydroxy-9-methyl-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of tert-butyl 7-benzyl-9-hydroxy-9-methyl-3,7-diazabicyclo-[3.3.1]nonane-3-carboxylate (from step (iii) above; 450 mg, 1.3 mmol) in aqueous ethanol (50 mL of 95%) was hydrogenated over 5% Pd/C at 1 atm until tlc indicated that the reaction was complete. The catalyst was removed by filtration through a pad of Celite®, and the filtrate concentrated under reduced pressure to give the sub-title compound in quantitative yield.

Workup

  1. customThe catalyst was removed by filtration through a pad of Celite®
  2. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-c5e4347b8e1b4ece86383663d03ac1cc
Source dataset
uspto-grants-2005_05
Patent number
US06887881B1

Reaction notes

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