Sodium Hydroxide → tert-Butyl (1R,3s,5S)-9-azabicyclo[3.3.1]nonan-3-ylcarbaMate

HRID 2059693Notes

Reaction equation

HRID 2059693 reaction equation
C[N:2]1[CH:7]2[CH2:8][CH2:9][CH2:10][CH:3]1[CH2:4][CH:5]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:6]2.[OH-].[Na+].[O-][Mn](=O)(=O)=O.[K+]>C1COCC1.O>[CH:7]12[NH:2][CH:3]([CH2:10][CH2:9][CH2:8]1)[CH2:4][CH:5]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:16])([CH3:15])[CH3:17])[CH2:6]2

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 516875Potassium Permanganate2×HCID 65471105HCID 65471105, compound

Product 1

HCID 45792693tert-Butyl (1R,3s,5S)-9-azabicyclo[3.3.1]nonan-3-ylcarbaMateYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the carbamate from Step A (430 mg, 1.69 mmol) in THF (2 mL) at 0° C. was added a solution of sodium hydroxide (2.0 g, 50 mmol) in water (20 mL), followed by a solution of KMnO4 (2.0 g, 12.6 mmol) in water (100 mL). The mixture was allowed to warm to room temperature and stirred overnight. Additional KMnO4 (2.0 g, 12.6 mmol) solution was added at room temperature and the mixture was stirred for additional 1 h. The mixture was extracted with methylene chloride. The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated to afford tert-butyl 9-azabicyclo[3.3.1]nonan-3-ylcarbamate (360 mg, 89%) as an off-white solid: 1H NMR (500 MHz, CDCl3) δ 4.32 (br s, 1H), 3.66 (br s, 1H), 3.33-3.00 (m, 2H), 2.25-2.00 (m, 2H), 1.85-1.48 (m, 5H), 1.45 (s, 9H), 1.40-1.35 (m, 2H), 1.09-1.02 (m, 2H); MS (ESI+) m/z 241 (M+H).

Workup

  1. stirringthe mixture was stirred for additional 1 h
  2. extractionThe mixture was extracted with methylene chloride
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2f733e1e1fef43259ba4a8a95cf65251
Source dataset
uspto-grants-2012_10
Patent number
US08278301B2

Reaction notes

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