HCID 86598914, compound → HCID 86598915, compound

HRID 456762Notes

Reaction equation

HRID 456762 reaction equation
[N:1]([C@H:4]1[C@H:9]2[CH2:10][C@H:6]([C@@H:7]([C:18]([O:20][CH3:21])=[O:19])[N:8]2[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:5]1)=[N+]=[N-].[H][H]>CO.[Pd]>[NH2:1][C@H:4]1[C@H:9]2[CH2:10][C@H:6]([C@@H:7]([C:18]([O:20][CH3:21])=[O:19])[N:8]2[C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[CH2:5]1

Participants

5

Reactant 2

HCID 86598914HCID 86598914, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86598915HCID 86598915, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-tert-butyl 3-methyl (1R,3S,4S,6R)-6-azido-2-azabicyclo[2.2.1]heptane-2,3-dicarboxylate obtained in Example 29-2 (170 mg) in methanol (4 mL), was added 10% palladium on carbon (30 mg). The mixture was stirred under 1 atm of hydrogen for 1.5 hrs at room temperature. The resulting mixture was filtered through celite and washed with methanol. The filtrate and washings were evaporated in vacuo to give the target compound (155 mg).

Workup

  1. filtrationThe resulting mixture was filtered through celite
  2. washwashed with methanol
  3. customThe filtrate and washings were evaporated in vacuo

Sources & evidence

ORD record
ord-1631ec36249d42a099c49ec0bbae7c9c
Source dataset
uspto-grants-2007_03
Patent number
US07186731B2

Reaction notes

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