(+-)-3-Quinuclidinol → Quinuclidin-3-yl2-bromophenylcarbamate

HRID 2281257Notes

Reaction equation

HRID 2281257 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([OH:9])[CH2:2]2.[H-].[Na+].[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N:19]=[C:20]=[O:21]>C1COCC1>[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH:19][C:20](=[O:21])[O:9][CH:3]1[CH:4]2[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]2)[CH2:2]1

Participants

5

Reactant 3

HCID 15381(+-)-3-QuinuclidinolHCID 24758Sodium hydrideHCID 1370972-Bromophenyl isocyanate

Product 1

HCID 68327765Quinuclidin-3-yl2-bromophenylcarbamateYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of quinuclidin-3-ol (382 mg, 3.00 mmol) in THF (15 mL) was added NaH [60% dispersion in mineral oil](156 mg, 3.90 mmol) at room temperature. The mixture was stirred for 15 min and 2-bromophenyl isocyanate (594 mg, 3.00 mmol) was added under stirring. The resulting mixture was stirred at room temperature for 18 h, quenched with brine and extracted with EtOAc. The organic layers were combined, dried over Na2SO4 and concentrated. The resulting crude product was purified by silica gel column chromatography (EtOAc/methanol 3:1) to give the product quinuclidin-3-yl 2-bromophenylcarbamate as viscous oil (0.80 g, 82%).

Workup

  1. stirringunder stirring
  2. stirringThe resulting mixture was stirred at room temperature for 18 h
  3. customquenched with brine
  4. extractionextracted with EtOAc
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe resulting crude product was purified by silica gel column chromatography (EtOAc/methanol 3:1)

Sources & evidence

ORD record
ord-a04cc68ceed8444e8bff8a2f3ea6feee
Source dataset
uspto-grants-2015_09
Patent number
US09139580B2

Reaction notes

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