Trifluoroacetic acid → trans-3-(3-Cyclopentoxy-4-methoxyphenyl)-4-methoxycarbonyl-1-(phenylmethyl)pyrrolidine

HRID 1377756노트

반응식

HRID 1377756 반응식
CO[CH2:3][N:4]([CH2:12][Si](C)(C)C)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH:17]1([O:22][C:23]2[CH:24]=[C:25](/[CH:31]=[CH:32]/[C:33]([O:35][CH3:36])=[O:34])[CH:26]=[CH:27][C:28]=2[O:29][CH3:30])[CH2:21][CH2:20][CH2:19][CH2:18]1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH:17]1([O:22][C:23]2[CH:24]=[C:25]([C@H:31]3[C@H:32]([C:33]([O:35][CH3:36])=[O:34])[CH2:3][N:4]([CH2:5][C:6]4[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=4)[CH2:12]3)[CH:26]=[CH:27][C:28]=2[O:29][CH3:30])[CH2:18][CH2:19][CH2:20][CH2:21]1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 5702848methyl 3-(3-cyclopentoxy-4-methoxyphenyl)-E-propenoate

생성물 1

HCID 70091886trans-3-(3-Cyclopentoxy-4-methoxyphenyl)-4-methoxycarbonyl-1-(phenylmethyl)pyrrolidine수율 86%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of N-methoxymethyl-N-(phenylmethyl)trimethylsilylmethylamine (2.84 g, 12 mmol) and (E)-methyl 3-(3-cyclopentoxy-4-methoxyphenyl)prop-2-enoate (2.76 g, 10 mmol) in 20 mL of CH2Cl2 cooled to 0° C. was added a 1 mL of a 1M solution of trifluoroacetic acid. Stirring was continued for 12 hr, and the solution was partitioned between ether and sat. NaHCO3. The layers were separated and the aqueous layer was extracted ethyl acetate (2×). The combined organic layers were dried (K2CO3), filtered, and concentrated under reduced pressure to a pale yellow oil. Chromatography on silica gel (3:1, hexanes:ethyl acetate) provided trans-3-(3-cyclopentoxy-4-methoxyphenyl)-4-methoxycarbonyl-1-(phenylmethyl)pyrrolidine (3.5 g, 86%) as a colorless oil. 1H-NMR (300 MHz): δ 2.74-3.09 (m, 5), 3.67 (s, 3), 3.81 (s, 3), 4.75 (m, 1).

후처리

  1. customthe solution was partitioned between ether and sat. NaHCO3
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted ethyl acetate (2×)
  4. dry with materialThe combined organic layers were dried (K2CO3)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure to a pale yellow oil

출처 및 근거

ORD 기록
ord-8d85434bfed74dca969894ff5bc2722b
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05665754

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