Hydrochloric Acid → HCID 20271664, compound

HRID 484642Notes

Reaction equation

HRID 484642 reaction equation
[N:1]([CH:4]1[CH2:9][CH:8]2[CH2:10][CH2:11][CH:5]1[CH2:6][N:7]2[C:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[N+]=[N-].B#B.Cl>C1COCC1>[NH2:1][CH:4]1[CH2:9][CH:8]2[CH2:10][CH2:11][CH:5]1[CH2:6][N:7]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6328200DiboronHCID 20271676HCID 20271676, compound

Product 1

HCID 20271664HCID 20271664, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of (±) 5-azido-2-benzoyl-2-azabicyclo[2,2,2]octane (D3d) (3.3 g) in dry THF (100 ml) under nitrogen was added a solution of diborane in THF (50 ml, 1M solution) and the whole heated under reflux for 12 hours. On cooling, an excess of 5N HCl was added and the mixture heated on a steam bath for 2 hrs. Basification and saturation with K2CO3, extraction with CH2Cl2, drying (K2CO3), concentration and distillation afforded the (±)-5-amino-2-benzyl-2-azabicyclo[2,2,2]-octane (D4b) (2.7 g, 85%) bp 120°-140°/0.1 mm.

Workup

  1. temperaturethe whole heated
  2. temperatureunder reflux for 12 hours
  3. temperatureOn cooling
  4. temperaturethe mixture heated on a steam bath for 2 hrs
  5. extractionBasification and saturation with K2CO3, extraction with CH2Cl2
  6. customdrying
  7. concentration(K2CO3), concentration and distillation

Sources & evidence

ORD record
ord-518df8c8170f444e812387fd7dc1a16e
Source dataset
uspto-grants-1985_08
Patent number
US04533498

Reaction notes

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