(+-)-3-Quinuclidinol → Quinuclidin-3-yl3-bromophenylcarbamate

HRID 2281252Notes

Reaction equation

HRID 2281252 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:14]=[C:15]([N:19]=[C:20]=[O:21])[CH:16]=[CH:17][CH:18]=1>C1COCC1>[Br:12][C:13]1[CH:14]=[C:15]([NH:19][C:20](=[O:21])[O:9][CH:3]2[CH:4]3[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]3)[CH2:2]2)[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 15381(+-)-3-QuinuclidinolHCID 24758Sodium hydrideHCID 1410013-Bromophenyl isocyanate

Product 1

HCID 54521110Quinuclidin-3-yl3-bromophenylcarbamateYield 43.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of quinuclidin-3-ol (635 mg, 5.00 mmol) in THF (15 mL) was added NaH [60% dispersion in mineral oil](260 mg, 6.50 mmol) at room temperature. The mixture was stirred for 15 min and 3-bromophenyl isocyanate (990 mg, 5.00 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 crude product was purified by silica gel column chromatography (eluting with EtOAc/methanol 3:1) to give quinuclidin-3-yl 3-bromophenylcarbamate as a white solid (0.70 g, 43%).

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 crude product was purified by silica gel column chromatography (eluting with EtOAc/methanol 3:1)

Sources & evidence

ORD record
ord-005afce0200b40f9b5cb70ea685596d4
Source dataset
uspto-grants-2015_09
Patent number
US09139580B2

Reaction notes

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