1,2-Dichloroethane → 9H-fluoren-9-yl quinuclidine-3-carboxylate

HRID 1910514Notes

Reaction equation

HRID 1910514 reaction equation
Cl.[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]([C:10]([OH:12])=[O:11])[CH2:3]2.C(Cl)CCl.C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1.[CH:34]1[C:46]2[CH:45](O)[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[C:38]=2[CH:37]=[CH:36][CH:35]=1>C1COCC1>[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]([C:10]([O:12][CH:45]1[C:46]3[CH:34]=[CH:35][CH:36]=[CH:37][C:38]=3[C:39]3[C:44]1=[CH:43][CH:42]=[CH:41][CH:40]=3)=[O:11])[CH2:3]2

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 74318Fluoren-9-olHCID 757711-HydroxybenzotriazoleHCID 126734361-Azabicyclo(2.2.2)octane-3-carboxylic acid hydrochloride

Product 1

HCID 709257749H-fluoren-9-yl quinuclidine-3-carboxylateYield 63.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Quinuclidine-3-carboxylic acid hydrochloride (95 mg, 0.50 mmol), EDC (143 mg, 0.74 mmol), triethylamine (242 μl, 1.73 mmol), and HOBT (114 mg, 0.74 mmol) were dissolved in dry THF (5 ml). 9H-fluoren-9-ol (99 mg, 0.54 mmol) was dissolved in dry THF (2 ml) and then added to the reaction mixture. The resulting suspension was stirred at room temperature overnight. The mixture was evaporated, and the crude taken up with EtOAc and washed sequentially with water and sat. NaHCO3. The organic phase was dried over sodium sulfate, filtered. and evaporated under vacuum. The crude was purified by flash chromatography (DCM/MeOH=9/1) to afford 9H-fluoren-9-yl quinuclidine-3-carboxylate (102 mg, racemic mixture).

Workup

  1. additionadded to the reaction mixture
  2. customThe mixture was evaporated
  3. washwashed sequentially with water and sat. NaHCO3
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. customand evaporated under vacuum
  7. customThe crude was purified by flash chromatography (DCM/MeOH=9/1)

Sources & evidence

ORD record
ord-ff77864e6ac94ac28d8fe898269cf041
Source dataset
uspto-grants-2013_12
Patent number
US08604015B2

Reaction notes

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