Ammonium formate → 5,9-Bis-(hydroxymethyl)-1-oxa-4,7,10-triazacyclododecane

HRID 1733792Notes

Reaction equation

HRID 1733792 reaction equation
C([O:8][CH2:9][CH:10]1[CH2:21][NH:20][CH2:19][CH:18]([CH2:22][O:23]CC2C=CC=CC=2)[NH:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][NH:11]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[OH:8][CH2:9][CH:10]1[CH2:21][NH:20][CH2:19][CH:18]([CH2:22][OH:23])[NH:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][NH:11]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 194385445,9-Bis(benzyloxymethyl)-1-oxa-4,7,10-triazacyclododecane

Product 1

HCID 194385435,9-Bis-(hydroxymethyl)-1-oxa-4,7,10-triazacyclododecane

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

5,9-Bis(benzyloxymethyl)-1-oxa-4,7,10-triazacyclododecane (0.24 g, 0.6 mmol) was dissolved in methanol (10 ml). Ammonium formate (0.20 g, 3 mmol) and 10% Palladium on carbon (0.40 g) were added and the mixture was stirred under a nitrogen atmosphere at 50° C. for 16 hours. The catalyst was filtered off and washed with methanol (5 ml). The filtrate was evaporated and the 5,9-Bis-(hydroxymethyl)-1-oxa-4,7,10-triazacyclododecane was isolated as a colourless oil. Yield 0.12 g (86%).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with methanol (5 ml)
  3. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-19dfd367b3a24d1d981b8c484f77dd3f
Source dataset
uspto-grants-1996_07
Patent number
US05531978

Reaction notes

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