Dicyclohexylcarbodiimide → HCID 86688950, compound

HRID 404690Notes

Reaction equation

HRID 404690 reaction equation
[N:1]1([CH:7]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)[C:8]([OH:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.[N:41]12[CH2:48][CH2:47][CH:44]([CH2:45][CH2:46]1)[C@@H:43](O)[CH2:42]2>C1COCC1>[N:1]1([CH:7]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)[C:8]([O:10][C@@H:43]2[CH:44]3[CH2:47][CH2:48][N:41]([CH2:46][CH2:45]3)[CH2:42]2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 24259050HCID 24259050, compound

Product 1

HCID 86688950HCID 86688950, compoundYield 35.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(piperidin-1-yl)-2-(thiophen-2-yl)acetic acid (250 mg, 1.11 mmol), DCC (458 mg, 2.22 mmol), HOBT (300 mg, 2.22 mmol) and (R)-quinuclidin-3-ol (282 mg, 2.22 mmol) in dry THF (11.1 ml) was stirred at room temperature under nitrogen atmosphere for 24 hours. The pale pink suspension was filtered washing with THF (5 ml) and the pale pink solution was evaporated. The crude was purified by flash chromatography (DCM/MeOH=95/5+0.4% NH4OH) to obtain the title compound (132 mg, 35.6% yield) as a colorless oil.

Workup

  1. filtrationThe pale pink suspension was filtered
  2. washwashing with THF (5 ml)
  3. customthe pale pink solution was evaporated
  4. customThe crude was purified by flash chromatography (DCM/MeOH=95/5+0.4% NH4OH)

Sources & evidence

ORD record
ord-ac32862c986d46b0a8f8d542fc483342
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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