Triethylamine → 5-Hydroxymethyl-1,3-dihydro-isoindole-2-carboxylic acid benzyl ester

HRID 1406815ノート

反応式

HRID 1406815 の反応式
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][OH:11])=[CH:7][CH:8]=2)[CH2:3][NH:2]1.C(N(CC)CC)C.Cl[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21]>O1CCCC1>[CH2:23]([O:22][C:20]([N:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[C:6]([CH2:10][OH:11])[CH:5]=2)[CH2:1]1)=[O:21])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 19828514Isoindolin-5-ylmethanol

生成物 1

HCID 579902105-Hydroxymethyl-1,3-dihydro-isoindole-2-carboxylic acid benzyl ester収率 98%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of (2,3-dihydro-1H-isoindol-5-yl)-methanol (1.34 g, 9.0 mmol) in anhydrous tetrahydrofuran (50 ml) was warmed gently to aid dissolution and allowed to cool to room temperature. Triethylamine (1.5 ml, 10.8 mmol) was added and the stirred mixture was treated dropwise with benzyl chloroformate (1.35 ml, 9.5 mmol) and stirred at room temperature for 3 hours. The solvent was removed in vacuo and the residue partitioned between ethyl acetate (30 ml) and 2M hydrochloric acid (30 ml). The organic layer was washed with water (30 ml), separated and the solvent removed in vacuo to afford a pink oil that solidified upon standing. The solids were triturated with 10% ethyl acetate in hexane (10 ml), filtered, rinsed with heptane (10 ml) and sucked dry to afford the title compound (2.5 g, 98%) as a pale pink solid. 1H NMR (DMSO-d6) 7.45-7.21 (8H, m), 5.20 (1H, t), 5.17 (2H, s), 4.71 (2H, br s), 4.64 (2H, br s), 4.50 (2H, d). MS: [M+H]+ 284.

後処理

  1. temperaturewas warmed gently
  2. dissolutiondissolution
  3. customThe solvent was removed in vacuo
  4. customthe residue partitioned between ethyl acetate (30 ml) and 2M hydrochloric acid (30 ml)
  5. washThe organic layer was washed with water (30 ml)
  6. customseparated
  7. customthe solvent removed in vacuo
  8. customto afford a pink oil
  9. customThe solids were triturated with 10% ethyl acetate in hexane (10 ml)
  10. filtrationfiltered
  11. washrinsed with heptane (10 ml)
  12. customsucked dry

出典と根拠

ORDレコード
ord-d223470a07e24c04b8cb66d9c42c96cd
出典データセット
uspto-grants-2014_12
特許番号
US08916552B2

反応ノート

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