1,2-Dichloroethane → (2-Chlorophenyl)(4-chlorophenyl)methyl quinuclidine-3-carboxylate

HRID 1910510

반응식

HRID 1910510 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.[Cl:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH:34]([C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=1)O.C(N(CC)CC)C>C1COCC1>[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]([C:10]([O:12][CH:34]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[Cl:27])[C:36]1[CH:37]=[CH:38][C:39]([Cl:42])=[CH:40][CH:41]=1)=[O:11])[CH2:3]2

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 247332(2-Chlorophenyl)(4-chlorophenyl)methanolHCID 126734361-Azabicyclo(2.2.2)octane-3-carboxylic acid hydrochloride

생성물 1

HCID 70925811(2-Chlorophenyl)(4-chlorophenyl)methyl quinuclidine-3-carboxylate수율 19.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Quinuclidine-3-carboxylic acid hydrochloride (0.1 g, 0.52 mmol), EDC (150 mg, 0.78 mmol), and HOBT (120 mg, 0.78 mmol) were dissolved in dry THF (3 ml). (2-Chlorophenyl)(4-chlorophenyl)methanol (145 mg, 0.57 mmol) was dissolved in dry THF (2 ml) and then added to the reaction mixture. Triethylamine (253 μl, 1.83 mmol) was added, and the resulting reaction was stirred at room temperature overnight. The mixture was evaporated, and the crude was taken up with EtOAc and washed with water and brine. The organic phase was separated, dried (sodium sulfate), filtered, and evaporated under vacuum. The crude was purified by flash chromatography (DCM/MeOH=95/5) to afford (2-chlorophenyl)(4-chlorophenyl)methyl quinuclidine-3-carboxylate (40 mg, mixture of diastereoisomers). The compound was used as such in the next step.

후처리

  1. additionadded to the reaction mixture
  2. customthe resulting reaction
  3. customThe mixture was evaporated
  4. washwashed with water and brine
  5. customThe organic phase was separated
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. customevaporated under vacuum
  9. customThe crude was purified by flash chromatography (DCM/MeOH=95/5)

출처 및 근거

ORD 기록
ord-eff852acc5e1415c8c3eebe1ea251ff5
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604015B2

연결된 노트

불러오는 중…