Dicyclohexylcarbodiimide → HCID 86688947, compound

HRID 404687Notes

Reaction equation

HRID 404687 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]([N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[C:10]([OH:12])=[O:11].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>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]([N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[C:10]([O:12][C@@H:46]1[CH:47]2[CH2:50][CH2:51][N:44]([CH2:49][CH2:48]2)[CH2:45]1)=[O:11]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 16243946HCID 16243946, compound

Product 1

HCID 86688947HCID 86688947, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(2,4-Difluorophenyl)-2-(piperidin-1-yl)acetic acid (304 mg, 1.19 mmol), DCC (491 mg, 2.38 mmol), and HOBT (365 mg, 2.38 mmol) were dissolved in dry THF (12 ml). (R)-quinuclidin-3-ol (454 mg, 3.57 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. The organic phase was dried over Na2SO4, filtered and evaporated to dryness. The crude was purified by flash chromatography (DCM/MeOH=9/1+0.1% NH4OH) to obtain the title product as colorless oil (280 mg, 64.5% yield).

Workup

  1. customTHF was evaporated
  2. washwashed with sat. NaHCO3
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude was purified by flash chromatography (DCM/MeOH=9/1+0.1% NH4OH)

Sources & evidence

ORD record
ord-780ec05ece8743a28d2e4c5ccb1f3a81
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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