1,2-Dichloroethane → Benzhydryl quinuclidine-3-carboxylate

HRID 1910507

반응식

HRID 1910507 반응식
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:27]1([CH:33]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C.CCOCC>[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]([C:10]([O:12][CH:33]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:11])[CH2:3]2

참가 물질

9

반응물 6

HCID 111,2-Dichloroethane2회HCID 7037BenzhydrolHCID 757711-Hydroxybenzotriazole2회HCID 81531Diisopropylethylamine2회HCID 516892Sodium BicarbonateHCID 126734361-Azabicyclo(2.2.2)octane-3-carboxylic acid hydrochloride2회

생성물 1

HCID 70926085Benzhydryl quinuclidine-3-carboxylate수율 31.1%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

Quinuclidine-3-carboxylic acid hydrochloride (114 mg, 0.60 mmol), EDC (156 mg, 0.81 mmol), and HOBT (125 mg, 0.81 mmol) were suspended in dry DMF (5 ml). Diphenylmethanol (100 mg, 0.54 mmol) and DIPEA (332 μl, 1.90 mmol) were added, and the mixture was stirred at room temperature for 24 hours. Quinuclidine-3-carboxylic acid hydrochloride (52.0 mg, 0.27 mmol), EDC (52.0 mg, 0.27 mmol), and HOBT (41.6 mg, 0.27 mmol) followed by DIPEA (95 μl, 0.54 mmol) were added again, and the mixture was stirred for 4 days. The reaction was then portioned between sat. NaHCO3 and Et2O. The organic layer was separated, washed again with sat. NaHCO3, water and brine, dried over Na2SO4, filtered, and evaporated to afford benzhydryl quinuclidine-3-carboxylate (54 mg, racemic mixture). The compound was used as such in the next step.

후처리

  1. additionwere added again
  2. stirringthe mixture was stirred for 4 days
  3. customThe organic layer was separated
  4. washwashed again with sat. NaHCO3, water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

출처 및 근거

ORD 기록
ord-eff67eb648aa4ff1bc159a4e95e699b4
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604015B2

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