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]=1PS-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.
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