HCID 59189493、化合物 → HCID 86639081、化合物

HRID 456328ノート

反応式

HRID 456328 の反応式
[C@:1]12([CH3:13])[C:7]([CH3:9])([CH3:8])[CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[C:10](Cl)=[O:11].[I:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([OH:26])[C:22]([CH3:25])([CH3:24])[CH3:23])=[C:17]([N+:27]([O-:29])=[O:28])[CH:16]=1>CN(C1C=CN=CC=1)C.ClCCl>[C@:1]12([CH3:13])[C:7]([CH3:9])([CH3:8])[CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[C:10]([O:26][CH:21]([C:18]1[CH:19]=[CH:20][C:15]([I:14])=[CH:16][C:17]=1[N+:27]([O-:29])=[O:28])[C:22]([CH3:24])([CH3:25])[CH3:23])=[O:11]

参加物

5

反応物 2

HCID 59189493HCID 59189493、化合物HCID 71432218(1s)-Camphanoyl chloride

生成物 1

HCID 86639081HCID 86639081、化合物収率 91%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

Under a nitrogen atmosphere, (1S)-camphanic acid chloride (1.68 g, 7.77 mmol) was added to a solution of (RS)-1-(4-iodo-2-nitrophenyl)-2,2-dimethyl-1-propanol (2.17 g, 6.47 mmol) and DMAP (1.18 g, 9.7 mmol) in anhydrous dichloromethane (50 mL). The mixture was stirred overnight at room temperature and then washed with saturated NaHCO3 solution (60 mL) and water (60 mL). The organic phase was dried over Na2SO4, concentrated in vacuo and purified by silica gel column chromatography to yield (RS)-1-(4-iodo-2-nitrophenyl)-2,2-dimethyl-1-propyl (1S)-camphanate (2.94 g, 88%, 1:1 mixture of diastereomers) as a white solid. 1H NMR (400 MHz, CDCl3) for diastereomers: δ 8.23 (m, 1 H, Ph-H), 7.90 (m, 1 H, Ph-H), 7.31 (m, 1 H, Ph-H), 6.56 and 6.51 (2 s, 1 H, Ph-CH), 2.38 (m, 1H), 2.07-1.9 (m, 2H), 1.69 (m, 1H), 1.13, 1.11, 1.07, 1.04, 1.02, 0.87 (6 s, 9 H, CH3×3), 0.96 (s, 9 H, (CH3)3C).

後処理

  1. washwashed with saturated NaHCO3 solution (60 mL) and water (60 mL)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. custompurified by silica gel column chromatography

出典と根拠

ORDレコード
ord-54f98c23035c4f86a21c9236daa5d142
出典データセット
uspto-grants-2013_07
特許番号
US08497360B2

反応ノート

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