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

HRID 334993노트

반응식

HRID 334993 반응식
[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

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydride2회HCID 23301778Methyl 2-benzylisoindoline-5-carboxylate

생성물 1

HCID 19828502(2-Benzylisoindolin-5-yl)methanol수율 99%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3b7050657a1b41c9803926bc053c4324
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883790B2

반응 노트

불러오는 중…