1,1-Dimethylethyl 10-(phenylmethyl)-3,10-diazabicyclo[4.3.1]decane-3-carboxylate → tert-butyl 3,10-diazabicyclo[4.3.1]decane-3-carboxylate

HRID 1946856Notes

Reaction equation

HRID 1946856 reaction equation
C([N:8]1[CH:14]2[CH2:15][CH2:16][CH2:17][CH:9]1[CH2:10][N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:12][CH2:13]2)C1C=CC=CC=1>CCO.[Pd]>[C:18]([N:11]1[CH2:12][CH2:13][CH:14]2[NH:8][CH:9]([CH2:17][CH2:16][CH2:15]2)[CH2:10]1)([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]

Participants

4

Reactant 1

HCID 684512181,1-Dimethylethyl 10-(phenylmethyl)-3,10-diazabicyclo[4.3.1]decane-3-carboxylate

Product 1

HCID 45792700tert-butyl 3,10-diazabicyclo[4.3.1]decane-3-carboxylateYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 10-benzyl-3-Boc-3,10-diazabicyclo-[4.3.1]decane obtained in Example 11 (3.50 g) in EtOH (52 ml) underwent hydrogenation at 45 psi and 30° C. for 19 hours in the presence of Pd/C 10% (1.13 g). At the end the mixture was filtered on celite and the catalyst washed with EtOH. The solution was then concentrated. 2.44 g of a light oil corresponding to the compound 3-BOC-3,10-diazabicyclo[4.3.1]decane (12a) are obtained.

Workup

  1. filtrationAt the end the mixture was filtered on celite
  2. washthe catalyst washed with EtOH
  3. concentrationThe solution was then concentrated

Sources & evidence

ORD record
ord-6b853f8ab10b40e1a2929b5ef4dfecd3
Source dataset
uspto-grants-2013_03
Patent number
US08399457B2

Reaction notes

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