Dicyclohexylcarbodiimide → HCID 86688898, compound

HRID 404639Notes

Reaction equation

HRID 404639 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.Cl.[C:27]1([CH:33]([N:37]2[CH2:42][CH2:41][S:40][CH2:39][CH2:38]2)[C:34]([OH:36])=[O:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[N:43]12[CH2:50][CH2:49][CH:46]([CH2:47][CH2:48]1)[C@@H:45](O)[CH2:44]2>C1COCC1>[C:27]1([CH:33]([N:37]2[CH2:38][CH2:39][S:40][CH2:41][CH2:42]2)[C:34]([O:36][C@@H:45]2[CH:46]3[CH2:49][CH2:50][N:43]([CH2:48][CH2:47]3)[CH2:44]2)=[O:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 457923011214028-77-9

Product 1

HCID 86688898HCID 86688898, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

PS-DCC (loading: 1.25 mmol/g; 0.73 g, 0.91 mmol) was suspended in dry THF (9 ml). HOBT (0.14 g, 0.91 mmol), 2-phenyl-2-thiomorpholinoacetic acid hydrochloride (0.12 g, 0.46 mmol) and (R)-quinuclidin-3-ol (0.17 g, 1.37 mmol) were sequentially added. The mixture was shaken overnight. PS-DCC was filtered off and washed with EtOAc and THF. The solution was evaporated and the residue was portioned between EtOAc and water. The organic phase was washed with sat. NaHCO3, dried (Na2SO4), filtered and evaporated. The crude was purified by flash chromatography (DCM/MeOH=95/5 to 85/15) to obtain (R)-quinuclidin-3-yl 2-phenyl-2-thiomorpholinoacetate (70 mg, 44.2% yield) as a colorless oil.

Workup

  1. filtrationPS-DCC was filtered off
  2. washwashed with EtOAc and THF
  3. customThe solution was evaporated
  4. washThe organic phase was washed with sat. NaHCO3
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude was purified by flash chromatography (DCM/MeOH=95/5 to 85/15)

Sources & evidence

ORD record
ord-7f1bb71b96a14c849d8244640c03fb7a
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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