Aluminium lithium hydride → HCID 59497801、化合物

HRID 1011511ノート

反応式

HRID 1011511 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:17][C@H:18]2[CH2:22][CH2:21][CH2:20][C@H:19]2[C:23](OCC)=[O:24])(=[O:16])=[O:15])=[CH:10][CH:9]=1>O1CCCC1>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:17][C@@H:18]2[CH2:22][CH2:21][CH2:20][C@@H:19]2[CH2:23][OH:24])(=[O:15])=[O:16])=[CH:10][CH:9]=1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 90811846cis-Ethyl 2-(4-chlorophenylsulfonamido)cyclopentanecarboxylate

生成物 1

HCID 59497801HCID 59497801、化合物収率 100.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A 1.0 M solution of lithium aluminum hydride in tetrahydrofuran (9.36 mL, 9.36 mmol) was added dropwise to a solution of cis-ethyl 2-(4-chlorophenylsulfonamido)cyclopentanecarboxylate (2.07 g, 6.24 mmol) in 40 mL anhydrous tetrahydrofuran under nitrogen at 0° C. The reaction was then stirred for 1 h at room temperature, then quenched by the slow addition of 100 mL ethyl acetate. The reaction was partitioned between 600 mL ethyl acetate and 300 mL saturated ammonium chloride. The organic layer was dried on sodium sulfate and concentrated to yield 4-chloro-N-(cis-2-(hydroxymethyl)cyclopentyl)benzenesulfonamide (1.81 g, 100%). 1H NMR (400 MHz, CDCl3) δ ppm 7.77-7.85 (2H, m), 7.45-7.50 (2H, m), 5.38 (1H, d, J=7.05 Hz), 3.61-3.78 (3H, m), 2.04-2.15 (1H, m), 1.27-1.80 (7H, m). LC/MS R.T.=2.46 min; [M+H]+=290.10.

後処理

  1. customquenched by the slow addition of 100 mL ethyl acetate
  2. customThe reaction was partitioned between 600 mL ethyl acetate and 300 mL saturated ammonium chloride
  3. customThe organic layer was dried on sodium sulfate
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-4840887b7fa34988ad7c16830b6ae509
出典データセット
uspto-grants-2011_07
特許番号
US07977362B2

反応ノート

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