反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.[N:21]([C@H:24]1[C@H:31]2[C@H:27]([CH2:28][N:29]([CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:30]2)[CH2:26][CH2:25]1)=[N+]=[N-]>O1CCCC1>[CH2:32]([N:29]1[CH2:30][C@H:31]2[C@H:24]([NH2:21])[CH2:25][CH2:26][C@H:27]2[CH2:28]1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1参加物
反応条件
- 温度
- 80 °C
実験手順
Triphenylphosphine (4.49 g, 17.13 mmol) and water (1.234 mL, 68.5 mmol) were added successively to a mixture of (3aS,4R,6aR)-4-azido-2-benzyloctahydrocyclopenta[c]pyrrole (1.384 g, 5.71 mmol) in tetrahydrofuran (30 mL). The reaction was refluxed at 80° C. for 2 hours. The crude material was adsorbed onto silica gel and applied to a silica gel cartridge (Analogix®, Burlington, Wis., RS-40) and eluted with 1-10% methanol (2 N ammonia)/chloroform to give (3aS,4R,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine: 1H NMR (500 MHz, pyridine-d5) δ ppm 7.45 (d, J=7.4, 2H), 7.38 (t, J=7.5, 2H), 7.29 (t, J=7.3, 1H), 3.52 (s, 2H), 3.14 (dd, J=5.7, 10.7, 1H), 2.62-2.55 (m, 1H), 2.52 (dd, J=3.2, 9.0, 1H), 2.38-2.29 (m, 3H), 2.20-2.13 (m, 1H), 2.01-1.84 (m, 2H), 1.40-1.29 (m, 2H).
後処理
- wash, RS-40) and eluted with 1-10% methanol (2 N ammonia)/chloroform
出典と根拠
- ORDレコード
- ord-f767667b5a1d464c839bd083e3192dc5
- 出典データセット
- uspto-grants-2012_03
- 特許番号
- US08129417B2
関連ノート
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