Dicyclohexylcarbodiimide → HCID 86688905, compound

HRID 404647Notes

Reaction equation

HRID 404647 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]([OH:13])=[O:12])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.[N:45]12[CH2:52][CH2:51][CH:48]([CH2:49][CH2:50]1)[C@@H:47](O)[CH2:46]2>C1COCC1>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]([O:13][C@@H:47]2[CH:48]3[CH2:51][CH2:52][N:45]([CH2:50][CH2:49]3)[CH2:46]2)=[O:12])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 22685869HCID 22685869, compound

Product 1

HCID 86688905HCID 86688905, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-Acetylpiperazin-1-yl)-2-phenylacetic acid (238 mg, 0.91 mmol) was suspended in dry THF (9 ml) and, with stirring at room temperature under nitrogen atmosphere, DCC (374 mg, 1.81 mmol), HOBT (245 mg, 1.81 mmol) and (R)-quinuclidin-3-ol (231 mg, 1.81 mmol) were sequentially added. The reaction was reacted at the same temperature for three days. The solvent was evaporated and the crude was purified by flash chromatography (DCM/MeOH/NH4OH=97/3/0.3). The product was suspended in THF/Acetonitrile (2/1; 10 ml) and the white solid was filtered off. The colourless solution was evaporated obtaining (R)-quinuclidin-3-yl 2-(4-acetylpiperazin-1-yl)-2-phenylacetate (218 mg, 64.7% yield) as a off-white spongy solid.

Workup

  1. customThe reaction was reacted at the same temperature for three days
  2. customThe solvent was evaporated
  3. customthe crude was purified by flash chromatography (DCM/MeOH/NH4OH=97/3/0.3)
  4. filtrationthe white solid was filtered off
  5. customThe colourless solution was evaporated

Sources & evidence

ORD record
ord-45f5d0ec8b3e4a58bca71ec1d1df6bc8
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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