Tert-butyl 7-benzyl-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate → 3-Boc-9-oxa-3,7-diazabicyclo[3.3.1]nonane

HRID 8574Notes

Reaction equation

HRID 8574 reaction equation
C([N:8]1[CH2:15][CH:14]2[O:16][CH:10]([CH2:11][N:12]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13]2)[CH2:9]1)C1C=CC=CC=1>C(O)C.[Pd]>[CH:10]12[O:16][CH:14]([CH2:15][NH:8][CH2:9]1)[CH2:13][N:12]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:11]2

Participants

4

Reactant 1

HCID 18540372Tert-butyl 7-benzyl-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate

Product 1

HCID 185404123-Boc-9-oxa-3,7-diazabicyclo[3.3.1]nonane

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5.60 g (17.6 mmol) of tert-butyl 7-benzyl-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate are dissolved in 100 ml of ethanol, 1.00 g of 10% palladium on activated carbon is added, and hydrogenation is carried out at 100° C. and 100 bar. The catalyst is filtered off with suction, and the filtrate is concentrated, whereupon 3.80 g (94.5% of theory) of pure product crystallize out.

Workup

  1. customis carried out at 100° C.
  2. filtrationThe catalyst is filtered off with suction
  3. concentrationthe filtrate is concentrated, whereupon 3.80 g (94.5% of theory) of pure product
  4. customcrystallize out

Sources & evidence

ORD record
ord-b92eecbe9f48471a8d576bc9f782095e
Source dataset
uspto-grants-2006_08
Patent number
US07091198B1

Reaction notes

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