Dicyclohexylcarbodiimide → HCID 86688891, compound

HRID 404631Notes

Reaction equation

HRID 404631 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.Cl.[C:27]1([CH:33]([N:37]2[CH2:41][CH2:40][CH2:39][CH2:38]2)[C:34]([OH:36])=[O:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[N:42]12[CH2:49][CH2:48][CH:45]([CH2:46][CH2:47]1)[C@@H:44](O)[CH2:43]2>C1COCC1>[C:27]1([CH:33]([N:37]2[CH2:41][CH2:40][CH2:39][CH2:38]2)[C:34]([O:36][C@@H:44]2[CH:45]3[CH2:48][CH2:49][N:42]([CH2:47][CH2:46]3)[CH2:43]2)=[O:35])[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 6603112100390-49-6

Product 1

HCID 86688891HCID 86688891, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

PS-DCC (loading: 1.25 mmol/g; 0.99 g, 1.24 mmol) was suspended in dry THF (12 ml). HOBT (0.19 g, 1.24 mmol), 2-phenyl-2-(pyrrolidin-1-yl)acetic acid hydrochloride (0.15 g, 0.62 mmol) and (R)-quinuclidin-3-ol (0.24 g, 1.86 mmol) were sequentially added. The mixture was shaken overnight and then PS-DCC was filtered washing with EtOAc and THF. The solution was evaporated and the residue was dissolved in EtOAc (30 ml) and washed with water (15 ml) and with a sat. NaHCO3 (20 ml). The organic phase was dried (Na2SO4), filtered and evaporated. The crude was purified by flash chromatography (DCM/MeOH=92/8 to 85/15) to obtain (R)-quinuclidin-3-yl 2-phenyl-2-(pyrrolidin-1-yl)acetate (53 mg, 27.2% yield) as a colorless oil.

Workup

  1. filtrationPS-DCC was filtered
  2. washwashing with EtOAc and THF
  3. customThe solution was evaporated
  4. dissolutionthe residue was dissolved in EtOAc (30 ml)
  5. washwashed with water (15 ml) and with a sat. NaHCO3 (20 ml)
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude was purified by flash chromatography (DCM/MeOH=92/8 to 85/15)

Sources & evidence

ORD record
ord-872ed5fb0fbd4d428d92f49012389064
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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