HCID 11819806, compound → HCID 53836085, compound

HRID 1078931Notes

Reaction equation

HRID 1078931 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 (mp) 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-43156fc6a6f14cf3ad55fb8fc860f650
Source dataset
uspto-grants-1996_08
Patent number
US05550243

Reaction notes

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