(+-)-3-Quinuclidinol → 4-Nitrophenyl quinuclidin-3-yl carbonate

HRID 2281234Notes

Reaction equation

HRID 2281234 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([OH:9])[CH2:2]2.Cl[C:11]([O:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)=[O:12]>C1COCC1>[C:11](=[O:12])([O:9][CH:3]1[CH:4]2[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]2)[CH2:2]1)[O:13][C:14]1[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 15381(+-)-3-QuinuclidinolHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 585817304-Nitrophenyl quinuclidin-3-yl carbonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-quinuclidinol (3.00 g, 23.6 mmol) in THF (100 mL) was added 4-nitrophenyl chloroformate (5.94 g, 29.5). After stirring for 4 hours, the precipitate was filtered off, rinsed with THF and air dried on the frit under house vacuum. The filtercake was dissolved in ethyl acetate (150 mL) and washed with aqueous NaHCO3 (1×150 mL) and water (2×150 mL). The organic layer was dried (Na2SO4) and concentrated to afford crude 4-nitrophenyl quinuclidin-3-yl carbonate product, which was used in the next step without purification.

Workup

  1. filtrationthe precipitate was filtered off
  2. washrinsed with THF and air
  3. customdried on the frit under house vacuum
  4. dissolutionThe filtercake was dissolved in ethyl acetate (150 mL)
  5. washwashed with aqueous NaHCO3 (1×150 mL) and water (2×150 mL)
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9234d7285b1942a8b341faa2db5a6d14
Source dataset
uspto-grants-2015_09
Patent number
US09139580B2

Reaction notes

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