Tert-butyl[3-(7-benzyl-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)propyl]carbamate → Tert-butyl[3-(9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)propyl]carbamate

HRID 2078400Notes

Reaction equation

HRID 2078400 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:18][CH:17]2[O:19][CH:13]([CH2:14][N:15](CC3C=CC=CC=3)[CH2:16]2)[CH2:12]1)([CH3:4])([CH3:3])[CH3:2]>C(O)C.[OH-].[Pd+2].[OH-]>[C:1]([O:5][C:6](=[O:27])[NH:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:12][CH:13]2[O:19][CH:17]([CH2:16][NH:15][CH2:14]2)[CH2:18]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 15980224Tert-butyl[3-(7-benzyl-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)propyl]carbamate

Product 1

HCID 131728789Tert-butyl[3-(9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)propyl]carbamateYield 113.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

tert-Butyl[3-(7-benzyl-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)propyl]carbamate (0.85 g, 2.2 mmol; see Example 11 below) was dissolved in ethanol (10 mL). Palladium hydroxide (0.5 g) was then added and the reaction mixture was hydrogenated in Parr shaker under 2.45 bar pressure for 4 h. The reaction mixture was filtered and solvent concentrated under reduced pressure to give the title compound (0.71 g, 84%) as an orange solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationsolvent concentrated under reduced pressure

Sources & evidence

ORD record
ord-2f03b475a4ce420a907e67cb74033f6c
Source dataset
uspto-grants-2011_04
Patent number
US07928225B2

Reaction notes

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