Toluene → (e)-Tert-butyl 3-(trans-1-benzyl-4-(3-methoxyphenyl)pyrrolidin-3-yl)acrylate

HRID 84961ノート

反応式

HRID 84961 の反応式
C([N:8]1[CH2:12][C@@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)[C@H:10]([CH:21]=O)[CH2:9]1)C1C=CC=CC=1.[O:23]([C:28]([CH:30]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:29])[C:24]([CH3:27])([CH3:26])[CH3:25].[C:50]1([CH3:56])[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>>[CH2:56]([N:8]1[CH2:12][C@@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)[C@H:10](/[CH:21]=[CH:30]/[C:28]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:29])[CH2:9]1)[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1

参加物

4

反応物 3

HCID 1140TolueneHCID 256127tert-Butyl (triphenylphosphoranylidene) acetateHCID 87294101trans-1-Benzyl-4-(3-methoxyphenyl)pyrrolidine-3-carbaldehyde

生成物 1

HCID 131731906(e)-Tert-butyl 3-(trans-1-benzyl-4-(3-methoxyphenyl)pyrrolidin-3-yl)acrylate

実験手順

A mixture of Example 261C (1.86 g, 6.3 mmol) and t-butoxylcarbonylmethylenetriphenylphosphorane (2.37 g, 6.3 mmol) in toluene (15 mL) was heated at 110° C. for 1 hour. The volatiles were removed and the crude material was purified by silica gel column chromatography eluting with hexanes and ethyl acetate (3:1) to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.32 (m, 4H), 7.25 (m, 1H), 7.18 (d, J=8.4 Hz, 1H), 6.85 (m, 2H), 6.76 (d, J=15.3 Hz, 1H), 5.69-5.61 (m, 1H), 3.73 (s, 3H), 3.70 (d, J=15.0 Hz, 1H), 3.59 (d, J=15.0 Hz, 1H), 3.13 (m, 1H), 2.98 (m, 3H), 2.62 (m, 1H), 2.53 (m, 1H), 1.39 (s, 9H).

後処理

  1. customThe volatiles were removed
  2. customthe crude material was purified by silica gel column chromatography
  3. washeluting with hexanes and ethyl acetate (3:1)

出典と根拠

ORDレコード
ord-e52fe8d4a75f4a06841613c9eb58e8ed
出典データセット
uspto-grants-2014_09
特許番号
US08846951B2

反応ノート

読み込み中…