HCID 67490883, compound → HCID 58944935, compound

HRID 1917333Notes

Reaction equation

HRID 1917333 reaction equation
C(OC([N:11]1[CH2:18][C@H:17]2[C@:13]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])([CH2:14][CH2:15][CH2:16]2)[CH2:12]1)=O)C1C=CC=CC=1.[H][H]>[C].[Pd].CO>[C:23]([O:22][C:20]([NH:19][C:13]12[CH2:14][CH2:15][CH2:16][CH:17]1[CH2:18][NH:11][CH2:12]2)=[O:21])([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 2

HCID 67490883HCID 67490883, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58944935HCID 58944935, compoundYield 104.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A 10% palladium-carbon catalyst (about 50% wet, 114 mg) was added to a solution of (−)-(1R*,5S*)-3-benzyloxycarbonyl-1-(tert-butoxycarbonylamino)-3-azabicyclo[3.3.0]octane (569 mg, 1.579 mmol) in methanol (30 mL), and the mixture was stirred in a hydrogen atmosphere at room temperature for two hours. The catalyst was removed by filtration, and then the solvent was evaporated under reduced pressure to give crude 1-(tert-butoxycarbonylamino)-3-azabicyclo[3.3.0]octane (373 mg) as a colorless transparent gummy solid.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6b81949802864603a0fb3d561fcfa5e8
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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