Aluminium lithium hydride → (2-Benzylisoindolin-5-yl)methanol

HRID 334993ノート

反応式

HRID 334993 の反応式
[CH2:1]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:17](OC)=[O:18])[CH:14]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:1]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:17][OH:18])[CH:14]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydride2 回HCID 23301778Methyl 2-benzylisoindoline-5-carboxylate

生成物 1

HCID 19828502(2-Benzylisoindolin-5-yl)methanol収率 99%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Methyl 2-benzyl-2,3-dihydro-1H-isoindole-5-carboxylate (from above) was dissolved in anhydrous tetrahydrofuran (75 ml) and added dropwise over 15 minutes to a rapidly stirred suspension of lithium aluminium hydride (1.71 g, 45.0 mmol) in anhydrous tetrahydrofuran (75 ml). The mixture was stirred at room temperature for 2 hours whereupon excess lithium aluminium hydride was destroyed by the slow dropwise addition of 1M sodium sulphate solution (12 ml). The solids were removed by filtration, rinsed with ethyl acetate (2×50 ml) and sucked dry. The solvent was removed in vacuo to afford (2-benzyl-2,3-dihydro-1H-isoindol-5-yl)-methanol (7.15 g, 99%) as a tan solid. 1H NMR (DMSO-d6) 7.40-7.30 (4H, m), 7.28 (1H, m), 7.17-7.10 (3H, m), 5.10 (1H, t), 4.47 (2H, d), 3.85 (2H, s), 3.82 (2H, s), 3.80 (2H, s). MS: [M+H]+ 240.

後処理

  1. customwas destroyed by the slow dropwise addition of 1M sodium sulphate solution (12 ml)
  2. customThe solids were removed by filtration
  3. washrinsed with ethyl acetate (2×50 ml)
  4. customsucked dry
  5. customThe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-3b7050657a1b41c9803926bc053c4324
出典データセット
uspto-grants-2014_11
特許番号
US08883790B2

反応ノート

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