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

HRID 1910514

반응식

HRID 1910514 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.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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-ff77864e6ac94ac28d8fe898269cf041
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604015B2

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