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

HRID 1377756ノート

反応式

HRID 1377756 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8d85434bfed74dca969894ff5bc2722b
出典データセット
uspto-grants-1997_09
特許番号
US05665754

反応ノート

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