Dicyclohexylcarbodiimide → HCID 86688916, compound

HRID 404657Notes

Reaction equation

HRID 404657 reaction equation
[F:1][C:2]1([F:18])[CH2:7][CH2:6][N:5]([CH:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]([OH:11])=[O:10])[CH2:4][CH2:3]1.[N:19]12[CH2:26][CH2:25][CH:22]([CH2:23][CH2:24]1)[C@@H:21](O)[CH2:20]2.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1>C1COCC1>[F:18][C:2]1([F:1])[CH2:3][CH2:4][N:5]([CH:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]([O:11][C@@H:21]2[CH:22]3[CH2:25][CH2:26][N:19]([CH2:24][CH2:23]3)[CH2:20]2)=[O:10])[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 59540290HCID 59540290, compound

Product 1

HCID 86688916HCID 86688916, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(4,4-difluoropiperidin-1-yl)-2-phenylacetic acid (512 mg, 2.01 mmol), (R)-quinuclidin-3-ol (306 mg, 2.41 mmol), DCC (497 mg, 2.41 mmol) and HOBT (369 mg, 2.41 mmol) in THF (20 ml) was stirred at room temperature over a week-end. THF was evaporated, the crude was taken up with EtOAc and washed twice with 2M K2CO3 and then with brine. The organic phase was dried over Na2SO4, filtered and evaporated to dryness. The crude was purified by flash-chromatography (DCM/MeOH=9/1) to obtain the title compound (348 mg, 47.6% yield) as a yellow sticky oil.

Workup

  1. customTHF was evaporated
  2. washwashed twice with 2M K2CO3
  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)

Sources & evidence

ORD record
ord-2c3ab12076aa41a58ee307968ed50569
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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