Toluene → trans-3-(3-Cyclopentoxy-4-methoxyphenyl)-4-methoxycarbonyl-1-(methylethoxycarbonyl)pyrrolidine

HRID 1377771ノート

反応式

HRID 1377771 の反応式
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C@H:15]3[C@H:19]([C:20]([O:22][CH3:23])=[O:21])[CH2:18][NH:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26].C1(C)C=CC=CC=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C@H:15]3[C@H:19]([C:20]([O:22][CH3:23])=[O:21])[CH2:18][N:17]([C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26])[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

参加物

6

反応物 3

HCID 1140TolueneHCID 7917Isopropyl chloroformateHCID 70093357trans-3-(3-Cyclopentoxy-4-methoxyphenyl)-4-(methoxycarbonyl)pyrrolidine

生成物 1

HCID 44302363trans-3-(3-Cyclopentoxy-4-methoxyphenyl)-4-methoxycarbonyl-1-(methylethoxycarbonyl)pyrrolidine収率 44%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of trans-3-(3-cyclopentoxy-4-methoxyphenyl)-4-(methoxycarbonyl)pyrrolidine (500 mg, 1.57 mmol) in 4 mL of CH2Cl2 was added at 0° C. 4-dimethylaminopyridine (250 mg, 2.04 mmol), followed by isopropyl chloroformate (1.7 mL of a 1M toluene solution). After 16 hr the reaction was diluted with CH2Cl2 and washed with 1M H3PO4. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. Silica gel chromatography (2:1, hexanes:ethyl acetate) provided trans-3-(3-cyclopentoxy-4-methoxyphenyl)-4-methoxycarbonyl-1-(methylethoxycarbonyl)pyrrolidine as a white solid (280 mg, 44%). Anal. Calcd for C22H29NO6 : C, 65.17; H, 7.71; N, 3.45. Found: C, 65.16; H, 7.69; N, 3.43.

後処理

  1. washwashed with 1M H3PO4
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-12dacad1509d4e0db6433773533c2bbb
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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