Dicyclohexylcarbodiimide → HCID 86688894, compound

HRID 404635Notes

Reaction equation

HRID 404635 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.Cl.[O:27]1[CH2:32][CH2:31][N:30]([CH:33]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:34]([OH:36])=[O:35])[CH2:29][CH2:28]1.[N:43]12[CH2:50][CH2:49][CH:46]([CH2:47][CH2:48]1)[C@@H:45](O)[CH2:44]2>C1COCC1>[O:27]1[CH2:28][CH2:29][N:30]([CH:33]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=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])[CH2:31][CH2:32]1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 71432425(Morpholin-4-yl)(phenyl)acetic acid--hydrogen chloride (1/1)

Product 1

HCID 86688894HCID 86688894, compoundYield 23.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

PS-DCC (loading: 1.25 mmol/g; 0.93 g, 1.16 mmol) was suspended in dry THF (11.6 ml) and HOBT (0.18 g, 1.16 mmol), 2-morpholino-2-phenylacetic acid hydrochloride (0.15 g, 0.58 mmol) and (R)-quinuclidin-3-ol (0.22 g, 1.75 mmol) were sequentially added. The mixture was shaken overnight and then PS-DCC was filtered off washing with EtOAc and THF. The solution was evaporated and the residue was dissolved in EtOAc (30 ml) and washed with water and then with a sat. NaHCO3. The organic phase was 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-morpholino-2-phenylacetate (45 mg, 23.4% yield) as a colorless oil.

Workup

  1. filtrationPS-DCC was filtered off
  2. washwashing with EtOAc and THF
  3. customThe solution was evaporated
  4. dissolutionthe residue was dissolved in EtOAc (30 ml)
  5. washwashed with water
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude was purified by flash chromatography (DCM/MeOH=95/5 to 85/15)

Sources & evidence

ORD record
ord-5885a27c348d47319f5a4eb3e37036c2
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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