Triethylamine → HCID 68328080, compound

HRID 2281244Notes

Reaction equation

HRID 2281244 reaction equation
Cl[C:2](Cl)([O:4][C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[Br:13][C:14]1[CH:15]=[C:16]([CH2:20][NH2:21])[CH:17]=[CH:18][CH:19]=1.C(N(CC)CC)C.[N:29]12[CH2:36]C[CH:32]([CH2:33][CH2:34]1)[CH:31](O)[CH2:30]2>C1COCC1>[Br:13][C:14]1[CH:15]=[C:16]([CH:17]=[CH:18][CH:19]=1)[CH2:20][NH:21][C:5](=[O:11])[O:4][CH:2]1[CH:32]2[CH2:33][CH2:34][N:29]([CH2:30][CH2:31]2)[CH2:36]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 15381(+-)-3-QuinuclidinolHCID 94429TriphosgeneHCID 457587Benzenemethanamine, 3-bromo-

Product 1

HCID 68328080HCID 68328080, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred and cooled (0° C.) solution of triphosgene (0.80 g, 2.7 mmol) in THF (20 mL) was added, dropwise, a mixture of (3-bromophenyl)methanamine (1.0 g, 5.4 mmol) and triethylamine (1.08 g, 10.7 mmol) in THF (30 mL) over 2 h. After the addition was complete, the mixture was refluxed for 1 h and then cooled to room temperature. Quinuclidin-3-ol (1.40 g, 10.7 mmol) was added, and the mixture was refluxed for 18 h. The solvent was removed in vacuo, and the residue was dissolved in EtOAc, washed with water, dried over Na2SO4, and concentrated. The crude residue was purified by silica gel column chromatography (eluting with EtOAc/methanol=10/1) to give quinuclidin-3-yl 3-bromobenzylcarbamate as a colourless liquid (0.68 g, 37%).

Workup

  1. additionwas added
  2. additionAfter the addition
  3. temperaturethe mixture was refluxed for 1 h
  4. temperaturethe mixture was refluxed for 18 h
  5. customThe solvent was removed in vacuo
  6. dissolutionthe residue was dissolved in EtOAc
  7. washwashed with water
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customThe crude residue was purified by silica gel column chromatography (eluting with EtOAc/methanol=10/1)

Sources & evidence

ORD record
ord-483e2340512c4234933785d2aaf7787e
Source dataset
uspto-grants-2015_09
Patent number
US09139580B2

Reaction notes

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