1,2-Dichloroethane → HCID 70926098, compound

HRID 1910513Notes

Reaction equation

HRID 1910513 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.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.[F:34][C:35]1[CH:36]=[C:37]([CH2:41]O)[CH:38]=[CH:39][CH:40]=1>C1COCC1>[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]([C:10]([O:12][CH2:41][C:37]1[CH:38]=[CH:39][CH:40]=[C:35]([F:34])[CH:36]=1)=[O:11])[CH2:3]2

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 680083-Fluorobenzylic alcoholHCID 757711-HydroxybenzotriazoleHCID 126734361-Azabicyclo(2.2.2)octane-3-carboxylic acid hydrochloride

Product 1

HCID 70926098HCID 70926098, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Quinuclidine-3-carboxylic acid hydrochloride (95 mg, 0.50 mmol), EDC (143 mg, 0.74 mmol), HOBT (114 mg, 0.74 mmol), and triethylamine (242 μl, 1.73 mmol) were dissolved in dry THF (5 ml). (3-Fluorophenyl)methanol (68.8 mg, 0.54 mmol) was dissolved in dry THF (2 ml) and added to the reaction mixture. The resulting reaction was stirred at room temperature overnight. The volatiles were evaporated, and the crude was taken up with EtOAc and washed with water and then with sat. NaHCO3. The organic phase was separated, dried over sodium sulfate, filtered, and evaporated under vacuum to obtain 3-fluorobenzyl quinuclidine-3-carboxylate (120 mg, racemic mixture). The compound was used in the next step without any further purification.

Workup

  1. additionadded to the reaction mixture
  2. customThe resulting reaction
  3. customThe volatiles were evaporated
  4. washwashed with water
  5. customThe organic phase was separated
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated under vacuum

Sources & evidence

ORD record
ord-9911e5e584e14a839a1674099cac5725
Source dataset
uspto-grants-2013_12
Patent number
US08604015B2

Reaction notes

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