Iodoethane → HCID 68996667, compound

HRID 2059694Notes

Reaction equation

HRID 2059694 reaction equation
[CH2:1](I)[CH3:2].[CH:4]12[NH:12][CH:8]([CH2:9][CH2:10][CH2:11]1)[CH2:7][CH:6]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:5]2>C(Cl)Cl>[CH2:1]([N:12]1[CH:4]2[CH2:11][CH2:10][CH2:9][CH:8]1[CH2:7][CH:6]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18])[CH2:5]2)[CH3:2]

Participants

4

Reactant 2

HCID 6340IodoethaneHCID 45792693tert-Butyl (1R,3s,5S)-9-azabicyclo[3.3.1]nonan-3-ylcarbaMate

Product 1

HCID 68996667HCID 68996667, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl iodide (50 μL, 0.63 mmol) was added to a solution of the amine from Step B (100 mg, 0.42 mmol) in methylene chloride (2 mL) at 0° C. The mixture was allowed to warm to room temperature and stirred for 30 h. The mixture was quenched with a saturated solution of sodium bicarbonate and extracted with methylene chloride. The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated. The crude material was purified by column chromatography (silica gel, 90:9:1 ethyl acetate/methanol/concentrated ammonium hydroxide) to afford tert-butyl 9-ethyl-9-azabicyclo[3.3.1]nonan-3-ylcarbamate (50 mg, 45%) as a white solid: 1H NMR (500 MHz, CDCl3) δ 4.28 (br s, 1H), 3.99 (br s, 1H), 3.13-3.10 (m, 2H), 2.63 (q, J=7.0 Hz, 2H), 2.38-2.30 (m, 2H), 1.90-1.82 (m, 3H), 1.48-1.46 (m, 1H), 1.44 (s, 9H), 1.16-0.95 (m, 7H); MS (ESI+) m/z 269 (M+H).

Workup

  1. customThe mixture was quenched with a saturated solution of sodium bicarbonate
  2. extractionextracted with methylene chloride
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by column chromatography (silica gel, 90:9:1 ethyl acetate/methanol/concentrated ammonium hydroxide)

Sources & evidence

ORD record
ord-f7255b2a0e8f423bb43eb9a187f658b1
Source dataset
uspto-grants-2012_10
Patent number
US08278301B2

Reaction notes

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