(7R,8aS)-7-azido-octahydro-5,5-dimethylindolizine → (7R,8aS)-octahydro-5,5-dimethylindolizin-7-amine

HRID 633336Notes

Reaction equation

HRID 633336 reaction equation
[N:1]([C@@H:4]1[CH2:12][C@H:11]2[N:7]([CH2:8][CH2:9][CH2:10]2)[C:6]([CH3:14])([CH3:13])[CH2:5]1)=[N+]=[N-]>CO.[OH-].[OH-].[Pd+2]>[CH3:13][C:6]1([CH3:14])[CH2:5][C@H:4]([NH2:1])[CH2:12][C@H:11]2[N:7]1[CH2:8][CH2:9][CH2:10]2

Participants

4

Reactant 1

HCID 86704447(7R,8aS)-7-azido-octahydro-5,5-dimethylindolizine2×

Product 1

HCID 86704446(7R,8aS)-octahydro-5,5-dimethylindolizin-7-amine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of crude (7R,8aS)-7-azido-octahydro-5,5-dimethylindolizine (Compound 3-8) (assumed 8.7 g) and Pd(OH)2 (20% weight on carbon; 1.7 g) in MeOH (150 mL) was hydrogenated at 30 psi at room temperature for 6 hours. The reaction mixture was filtered through a pad of Celite and the filter cake was washed with MeOH (200 mL). The filtrate was concentrated under vacuum to give the product, which was used directly in the next step—yield assumed quantitative (7.5 g).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. washthe filter cake was washed with MeOH (200 mL)
  3. concentrationThe filtrate was concentrated under vacuum
  4. customto give the product, which
  5. customnext step—yield

Sources & evidence

ORD record
ord-57c0b91ef5e7464bac442647c405204c
Source dataset
uspto-grants-2016_04
Patent number
US09321763B2

Reaction notes

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