Dicyclohexylcarbodiimide → HCID 86688888, compound

HRID 404627Notes

Reaction equation

HRID 404627 reaction equation
Cl.[CH3:2][CH:3]1[CH2:8][CH2:7][N:6]([CH:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]([OH:12])=[O:11])[CH2:5][CH2:4]1.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.[N:44]12[CH2:51][CH2:50][CH:47]([CH2:48][CH2:49]1)[C@@H:46](O)[CH2:45]2>C1COCC1>[CH3:2][CH:3]1[CH2:8][CH2:7][N:6]([CH:9]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:10]([O:12][C@@H:46]2[CH:47]3[CH2:50][CH2:51][N:44]([CH2:49][CH2:48]3)[CH2:45]2)=[O:11])[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 16192951HCID 16192951, compound

Product 1

HCID 86688888HCID 86688888, compoundYield 43.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-Methylpiperidin-1-yl)-2-phenylacetic acid hydrochloride (105 mg, 0.39 mmol), HOBT (119 mg, 0.78 mmol), and DCC (161 mg, 0.78 mmol) were dissolved in dry THF (5 ml). (R)-quinuclidin-3-ol (149 mg, 1.17 mmol) was added and the reaction mixture was stirred at room temperature for 16 hours. THF was evaporated, the residue was dissolved in EtOAc and washed with sat. NaHCO3, water and brine. The organic layer was dried over Na2SO4, filtered and evaporated. The crude was purified by flash chromatography (DCM/MeOH=9/1) to obtain (R)-quinuclidin-3-yl 2-(4-methylpiperidin-1-yl)-2-phenylacetate (58 mg, 43.5% yield).

Workup

  1. customTHF was evaporated
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with sat. NaHCO3, water and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude was purified by flash chromatography (DCM/MeOH=9/1)

Sources & evidence

ORD record
ord-da4ad630604d460db2ffe7596faa0400
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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