Dicyclohexylcarbodiimide → HCID 86688936, compound

HRID 404674Notes

Reaction equation

HRID 404674 reaction equation
Cl.[N:2]1([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[C:9]([OH:11])=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.[N:44]12[CH2:51][CH2:50][CH:47]([CH2:48][CH2:49]1)[C@@H:46](O)[CH2:45]2>C1COCC1>[N:2]1([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[C:9]([O:11][C@@H:46]2[CH:47]3[CH2:50][CH2:51][N:44]([CH2:49][CH2:48]3)[CH2:45]2)=[O:10])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 86688935HCID 86688935, compound

Product 1

HCID 86688936HCID 86688936, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(Piperidin-1-yl)-2-p-tolylacetic acid hydrochloride (242 mg, 0.90 mmol), DCC (370 mg, 1.79 mmol) and HOBT (275 mg, 1.79 mmol) were dissolved in dry THF (10 ml). (R)-quinuclidin-3-ol (342 mg, 2.69 mmol) was added and the mixture was stirred at room temperature for 16 hours. THF was evaporated and the residue was taken up with EtOAc and washed with sat. NaHCO3, water and brine. The organic layer was recovered, dried over Na2SO4, filtered and evaporated. The crude was purified by flash chromatography (DCM/MeOH=9/1) to obtain (R)-quinuclidin-3-yl 2-(piperidin-1-yl)-2-p-tolylacetate (169 mg, 55% yield) as a colourless oil.

Workup

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

Sources & evidence

ORD record
ord-f9714fb48c7d4c2b9e1f6e50e226c22b
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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