Trifluoromethanesulfonic acid → (S)-(1-benzylpyrrolidin-3-yl)-[(R)-1-(3-methoxyphenyl)ethyl]amine

HRID 1811642

반응식

HRID 1811642 반응식
[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10](O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.FC(F)(F)S(O)(=O)=O.[CH3:31][O:32][C:33]1[CH:34]=[C:35]([C@H:39]([NH2:41])[CH3:40])[CH:36]=[CH:37][CH:38]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(Cl)(Cl)Cl>[CH2:1]([N:8]1[CH2:12][CH2:11][C@H:10]([NH:41][C@@H:39]([C:35]2[CH:36]=[CH:37][CH:38]=[C:33]([O:32][CH3:31])[CH:34]=2)[CH3:40])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

8

반응물 5

HCID 62406Trifluoromethanesulfonic acidHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 643472(R)-(+)-1-Benzyl-3-pyrrolidinolHCID 7020759(R)-1-(3-Methoxyphenyl)ethylamine

생성물 1

HCID 58973545(S)-(1-benzylpyrrolidin-3-yl)-[(R)-1-(3-methoxyphenyl)ethyl]amine수율 28.4%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6344Dichloromethane용매3회

반응 조건

온도
-20 °C

실험 절차

To a solution of 8.0 g of (R)-1-benzyl-3-pyrrolidinol and 16.5 ml of diisopropylethylamine dissolved in 400 ml of methylene chloride was added dropwise a solution of 13.4 g of anhydrous trifluoromethanesulfonic acid in 50 ml of a methylene chloride at −20° C. or lower. The reaction mixture was stirred for 15 minutes while maintaining it to −20° C., then, a solution of 9.88 g of (R)-1-(3-methoxyphenyl)ethylamine in 100 ml of methylene chloride was added dropwise to the mixture at −20° C. or lower, and the reaction mixture was stirred at room temperature for 16 hours. To the reaction mixture were added a saturated aqueous sodium bicarbonate solution and chloroform, the mixture was stirred and the liquids were separated. The organic layer was dried and concentrated, and the residue was purified by silica gel column chromatography (chloroform:methanol=1:0→50:1) and NH silica gel column chromatography (hexane:ethyl acetate=25:1→10:1) to obtain 3.98 g of (S)-(1-benzylpyrrolidin-3-yl)-[(R)-1-(3-methoxyphenyl)ethyl]amine.

후처리

  1. stirringlower, and the reaction mixture was stirred at room temperature for 16 hours
  2. stirringthe mixture was stirred
  3. customthe liquids were separated
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customthe residue was purified by silica gel column chromatography (chloroform:methanol=1:0→50:1) and NH silica gel column chromatography (hexane:ethyl acetate=25:1→10:1)

출처 및 근거

ORD 기록
ord-3d58c08dec5b4c2f8632e7c3be23bf3e
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362274B2

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