Dicyclohexylcarbodiimide → HCID 86688922, compound

HRID 404662Notes

Reaction equation

HRID 404662 reaction equation
[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C@H:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:8]([OH:10])=[O:9].C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.[N:42]12[CH2:49][CH2:48][CH:45]([CH2:46][CH2:47]1)[C@@H:44](O)[CH2:43]2.C(Cl)Cl.CO.[NH4+].[OH-]>C1COCC1>[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:8]([O:10][C@@H:44]1[CH:45]2[CH2:48][CH2:49][N:42]([CH2:47][CH2:46]2)[CH2:43]1)=[O:9]

Participants

7

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 21896990Dichloromethane methanol ammonium hydroxideHCID 86688923HCID 86688923, compound

Product 1

HCID 86688922HCID 86688922, compoundYield 21.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of (R)-2-((R)-2-methylpyrrolidin-1-yl)-2-phenylacetic acid 22c (150 mg, 0.68 mmol) in dry THF (6.8 ml), were added DCC (282 mg, 1.37 mmol), HOBT (185 mg, 1.37 mmol) and (R)-quinuclidin-3-ol (174 mg, 1.37 mmol). The mixture was stirred at room temperature under nitrogen for 24 hours. The pale yellow suspension was filtered washing with THF (5 ml) and the yellow solution was evaporated. The crude was purified by flash chromatography (DCM/MeOH=95/5 to 9/1 and then with DCM/MeOH/NH4OH=95/5/0.2) to collect the title compound (48 mg, 21.4% yield) as a colorless oil.

Workup

  1. filtrationThe pale yellow suspension was filtered
  2. washwashing with THF (5 ml)
  3. customthe yellow solution was evaporated
  4. customThe crude was purified by flash chromatography (DCM/MeOH=95/5 to 9/1

Sources & evidence

ORD record
ord-afdf287c8d7840b498608cd83c8fbccc
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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