HCID 19424454, compound → HCID 19424399, compound

HRID 743482Notes

Reaction equation

HRID 743482 reaction equation
C([NH:11][S:12]([N:15]1[CH:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:19]2[CH2:26][CH:16]1[CH2:17][CH2:18]2)(=[O:14])=[O:13])(OCC1C=CC=CC=1)=O>CO.[Pd]>[NH2:11][S:12]([N:15]1[CH:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:19]2[CH2:26][CH:16]1[CH2:17][CH2:18]2)(=[O:14])=[O:13]

Participants

4

Reactant 1

HCID 19424454HCID 19424454, compound

Product 1

HCID 19424399HCID 19424399, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of ethyl N-(carbobenzyloxyaminosulfonyl)-2-azabicyclo[2,2,1]heptan-3-carboxylate (40.35 g; 105.51 mmol) in methanol (300 ml) under nitrogen was cooled to 0° C. and 2.5 g of 10% Pd/C was added. The mixture was placed into a Parr Apparatus and hydrogenated for 3 hours at 50 psi. The catalyst was removed on a pad of CELITE® and the filtrate was concentrated in vacuo and purified by flash silica gel chromatography (35-40% ethyl acetate/hexane) to afford 22.79 g (87%) of ethyl N-(aminosulfonyl)-2-azabicyclo[2,2,1]heptan-3-carboxylate (Formula VII: R=Ethyl; R1 =H; R2 and R3 together = ##STR19## as a solid.

Workup

  1. customThe catalyst was removed on a pad of CELITE®
  2. concentrationthe filtrate was concentrated in vacuo
  3. custompurified by flash silica gel chromatography (35-40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-cb728aec84a449c587bb4dc620d05592
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

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