HCID 11819806, compound → HCID 53836085, compound

HRID 275012Notes

Reaction equation

HRID 275012 reaction equation
[N:1]([C@@H:4]1[C@@H:9]([OH:10])[C@H:8]([OH:11])[C@@H:7]([CH2:12][OH:13])[NH:6][CH2:5]1)=[N+]=[N-]>CO.[Pd]>[NH2:1][C@@H:4]1[C@@H:9]([OH:10])[C@H:8]([OH:11])[C@@H:7]([CH2:12][OH:13])[NH:6][CH2:5]1

Participants

4

Reactant 1

HCID 11819806HCID 11819806, compound

Product 1

HCID 53836085HCID 53836085, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 12 (465 mg, 3.14 mmol) in methanol (50 ml) in a Parr hydrogenation flask, 10% Pd on C (50 mg) was added. The system was sealed, purged with nitrogen (5 times) and hydrogen (5 times) and then pressurized to 5 psi hydrogen. After running the reaction on a shaker for 3.5 hr, the system was vented, purged with nitrogen and filtered. The filtrate was concentrated to give pure 20 (365 mg, 91%). DSC (top) 184° C. Anal calcd. for C6H14N2O3 0.25H2O C, 43.23, H, 8.77, N, 16.81 Found C, 43.42, H, 8.43,<N, 16.47.

Workup

  1. customThe system was sealed
  2. custompurged with nitrogen (5 times) and hydrogen (5 times)
  3. customthe reaction on a shaker for 3.5 hr
  4. custompurged with nitrogen
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-09d9c232c7524aeb98014d8b02d111e5
Source dataset
uspto-grants-1995_02
Patent number
US05391746

Reaction notes

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