Aluminium lithium hydride → (S)-benzyl 5-(hydroxymethyl)-2,3-dihydro-1H-inden-2-ylcarbamate

HRID 473104ノート

反応式

HRID 473104 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:21](OC)=[O:22])[CH:18]=2)[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[OH:22][CH2:21][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[CH2:13][C@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:20]2

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 67025433(S)-methyl 2-(benzyloxycarbonylamino)-2,3-dihydro-1H-indene-5-carboxylate

生成物 1

HCID 70224068(S)-benzyl 5-(hydroxymethyl)-2,3-dihydro-1H-inden-2-ylcarbamate収率 82%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To (S)-methyl 2-(benzyloxycarbonylamino)-2,3-dihydro-1H-indene-5-carboxylate (7.38 mmol, 2.4 g) at 0° C. in THF (36.9 mL) under an argon atmosphere was added Lithium aluminium hydride in THF (7.38 mmol, 7.38 mL) dropwise. The reaction was left to stir for 1.5 hrs at 0 degrees. The reaction was quenched with water before the addition of 5N HCl (aq) to adjust the pH to 3. DCM was added before separating the aqueous and washing once with water and once with brine. The DCM layer was dried over MgSO4 before removing the solvent in vacuo. The crude product was purified by silica chromatography (2:1 Heptane/EtOAc to 2:1 EtOAc/Heptane, 100 g silica cartridge) to give the product as a white solid (1.8 g, 82%). 1H NMR (400 MHz, CDCl3) δ 1.60 (t, 1H), 2.81 (m, 2H), 3.27 (m, 2H), 4.53 (d, 1H), 4.66 (d, 2H), 4.95 (brs, 1H), 5.12 (s, 2H), 7.17 (d, 2H), 7.23 (m, 1H), 7.33 (m, 5H).

後処理

  1. waitThe reaction was left
  2. customThe reaction was quenched with water before the addition of 5N HCl (aq)
  3. additionDCM was added
  4. custombefore separating the aqueous and
  5. washwashing once with water and once with brine
  6. dry with materialThe DCM layer was dried over MgSO4
  7. custombefore removing the solvent in vacuo
  8. customThe crude product was purified by silica chromatography (2:1 Heptane/EtOAc to 2:1 EtOAc/Heptane, 100 g silica cartridge)

出典と根拠

ORDレコード
ord-3aad87eb262c450f9240905618a42c4a
出典データセット
uspto-grants-2014_01
特許番号
US08633237B2

反応ノート

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