Dicyclohexylcarbodiimide → HCID 86688919, compound

HRID 404660Notes

Reaction equation

HRID 404660 reaction equation
[N:1]1([CH:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]([OH:11])=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N:18]12[CH2:25][CH2:24][CH:21]([CH2:22][CH2:23]1)[C@@H:20](O)[CH2:19]2.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1>[N:1]1([CH:8]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:9]([O:11][C@@H:20]2[CH:21]3[CH2:24][CH2:25][N:18]([CH2:23][CH2:22]3)[CH2:19]2)=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 20992498HCID 20992498, compound

Product 1

HCID 86688919HCID 86688919, compoundYield 15.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(azepan-1-yl)-2-phenylacetic acid (476 mg, 2.04 mmol), (R)-quinuclidin-3-ol (311 mg, 2.45 mmol), HOBT (375 mg, 2.45 mmol) and DCC (505 mg, 2.45 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=95/5) to get (R)-quinuclidin-3-yl 2-(azepan-1-yl)-2-phenylacetate (110 mg, 15.7% yield) as a white solid.

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=95/5)

Sources & evidence

ORD record
ord-81284398dea64387b9cb08aec32330c2
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

Loading…