(1R,2R,3R,5R,6R)-2,3-diazido-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester → (1R,2R,3R,5R,6R)-2,3-diamino-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester

HRID 130506Notes

Reaction equation

HRID 130506 reaction equation
[CH2:1]([O:3][C:4]([C@:6]1([N:21]=[N+]=[N-])[C@H:11]([N:12]=[N+]=[N-])[CH2:10][C@@H:9]2[C@H:7]1[C@@:8]2([F:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:5])[CH3:2]>C(O)(=O)C.O.[C].[Pd]>[CH2:1]([O:3][C:4]([C@:6]1([NH2:21])[C@H:11]([NH2:12])[CH2:10][C@@H:9]2[C@H:7]1[C@@:8]2([F:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:5])[CH3:2]

Participants

5

Reactant 1

HCID 86606016(1R,2R,3R,5R,6R)-2,3-diazido-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester

Product 1

HCID 11311858(1R,2R,3R,5R,6R)-2,3-diamino-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl esterYield 29.4%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

25 mg of 10% palladium carbon was added to 170 mg of (1R,2R,3R,5R,6R)-2,3-diazido-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester dissolved in a mixture of 15 mL of acetic acid and 5 mL of water, and the mixture was stirred for 24 hours at room temperature under a hydrogen atmosphere. After celite filturation, the solvent was distilled off at 50° C. under reduced pressure, thereby yielding 42 mg of (1R,2R,3R,5R,6R)-2,3-diamino-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester.

Workup

  1. distillationAfter celite filturation, the solvent was distilled off at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-4c31a4d73fc347aaa6a3bd07a0431aef
Source dataset
uspto-grants-2008_06
Patent number
US07381746B2

Reaction notes

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