Tetrahydrofuran → HCID 131731998, compound

HRID 332651Notes

Reaction equation

HRID 332651 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10](=[O:39])[N:11]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21](OCCCCCCCCC3OCCO3)[CH:20]=1)[CH2:12][C:13]1[CH:18]=CC=[CH:15][CH:14]=1)[CH2:2]2.[C:40](=[O:43])([O-])[O-].[K+].[K+].[CH2:46]1[CH2:50][O:49][CH2:48][CH2:47]1>Cl>[N:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[C@@H:3]([O:9][C:10](=[O:39])[N:11]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH2:12][C:13]1[CH:14]=[CH:15][CH:46]=[C:50]([O:49][CH2:48][CH2:47][CH2:23][CH2:24][CH2:19][CH2:20][CH2:21][CH2:22][CH:40]=[O:43])[CH:18]=1)[CH2:2]2

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 131731999HCID 131731999, compound

Product 1

HCID 131731998HCID 131731998, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a stirred solution of (R)-quinuclidin-3-yl(3-(8-(1,3-dioxolan-2-yl)octyloxy)phenyl)(phenyl)methylcarbamate (0.66 g, 1.23 mmol) in THF (10 mL), 2M hydrochloric acid was added (20 mL). The reaction mixture was stirred at RT for 3 hours. To the reaction mixture was added 10% aqueous potassium carbonate, and the mixture extracted with DCM (×3). The combined organic extracts were washed poured through a hydrophobic cartridge, and concentrated under reduced pressure to afford the title compound (0.64 g, quantitative yield). The material was used directly in the next step with no further purification.

Workup

  1. extractionthe mixture extracted with DCM (×3)
  2. washThe combined organic extracts were washed
  3. additionpoured through a hydrophobic cartridge
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ed3e9f90e57f4950914c4e5d7362bbf4
Source dataset
uspto-grants-2014_11
Patent number
US08877774B2

Reaction notes

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