Pyridine → HCID 117833033, compound

HRID 516653Notes

Reaction equation

HRID 516653 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[CH3:13][C:14]12[NH:22][C:18]([CH3:23])([CH2:19][CH2:20][CH2:21]1)[CH2:17][C:16](=[O:24])[CH2:15]2.N1C=CC=CC=1.[C:31]([OH:35])([CH3:34])([CH3:33])[CH3:32]>O.ClCCl>[C:31]([O:35][C:2]([N:22]1[C:18]2([CH3:23])[CH2:19][CH2:20][CH2:21][C:14]1([CH3:13])[CH2:15][C:16](=[O:24])[CH2:17]2)=[O:4])([CH3:34])([CH3:33])[CH3:32]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6386tert-ButanolHCID 94429TriphosgeneHCID 117832979HCID 117832979, compound

Product 1

HCID 117833033HCID 117833033, compoundYield 113.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Triphosgene (1.33 g, 4.48 mmol) was added in several portions to a dichloromethane solution (50 ml) of 1,5-dimethyl-9-azabicyclo[3.3.1]nonan-3-one (1.87 g, 11.2 mmol) and pyridine (2.3 ml, 28 mmol) under ice-cooled condition. After stirring the mixture for 30 min under ice-cooled condition, tert-butanol (2.2 ml, 22.4 mmol) was dropped, and the mixture was stirred for 8 h. The reaction was stopped by adding water to the reaction liquid. The reaction liquid was then extracted with diethyl ether, washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography, and N-tert-butoxycarbonyl-1,5-dimethyl-9-azabicyclo[3.3.1]nonan-3-one (0.37 g, 13%), and 1,5-dimethyl-9-azabicyclo[3.3.1]nonan-3-one (1.1 g, 59%) were collected. The collected 1,5-dimethyl-9-azabicyclo[3.3.1]nonan-3-one was subjected to the same procedure twice to give N-tert-butoxycarbonyl-1,5-dimethyl-9-azabicyclo[3.3.1]nonan-3-one (1.36 g, 44%).

Workup

  1. temperaturecooled condition
  2. additionwas dropped
  3. stirringthe mixture was stirred for 8 h
  4. customto the reaction liquid
  5. customThe reaction liquid
  6. extractionwas then extracted with diethyl ether
  7. washwashed with saturated brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography, and N-tert-butoxycarbonyl-1,5-dimethyl-9-azabicyclo[3.3.1]nonan-3-one (0.37 g, 13%), and 1,5-dimethyl-9-azabicyclo[3.3.1]nonan-3-one (1.1 g, 59%)
  11. customwere collected

Sources & evidence

ORD record
ord-fcbaad45e4fb409b992e2c0e3105ed3c
Source dataset
uspto-grants-2015_08
Patent number
US09114390B2

Reaction notes

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