Sodium Iodide → HCID 86625664、化合物

HRID 68199ノート

反応式

HRID 68199 の反応式
[C:1]([N:5]([CH:17]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:18]([CH3:20])[CH3:19])[O:6][CH:7]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15]Cl)=[CH:11][CH:10]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[I-:27].[Na+]>CC(C)=O>[C:1]([N:5]([CH:17]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:18]([CH3:20])[CH3:19])[O:6][CH:7]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][I:27])=[CH:11][CH:10]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 5238Sodium IodideHCID 22733773N-tert-Butyl-O-[1-[4-(chloromethyl)phenyl]ethyl]-N-(2-methyl-1-phenylpropyl)hydroxylamine

生成物 1

HCID 86625664HCID 86625664、化合物

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a 50-mL round-bottom flask equipped with a magnetic stirbar was added chloromethyl alkoxyamine 3 (1.789 g, 4.784 mmol) and acetone (20 mL). To the resulting solution was added sodium iodide (2.869 g, 19.14 mmol, 4 equiv) and the reaction mixture was capped with a rubber septum and allowed to stir for 24 hours at room temperature. The sodium chloride side product was remove by gravity filtration, and the filtrate was concentrated on a rotary evaporator. The crude oily product was purified by flash chromatography, eluting with hexanes. The desired iodomethyl akoxyamine 4 was obtained as a colorless oil (1.968 g, 88.3% yield). ESI-MS: m/z=466.0, observed; 465.41, calculated. 1H NMR (500 MHz, CDCl3, both diastereomers) δ 7.5-7.1 (m, 18H), 5.35 (t, 2H) 4.90 (q+q, 2H, both diastereomers), 4.55 (s, 4H), 3.55 (m, 2H), 3.40 (d, 1H, minor diastereomer), 3.30 (d, 1H, major diastereomer), 2.40 (m, 2H, both diastereomer), 2.30 (d, 2H), 1.65 (d, 3H, minor diastereomer), 1.58 (d, 3H, major diastereomer), 1.33 (d, 3H, minor diastereomer), 1.05 (s, 9H, major diastereomer), 0.98 (s, 6H), 0.95 (d, 3H, major diastereomer), 0.89 (d, 12H), 0.85 (d, 6H), 0.82 (s, 9H, minor diastereomer), 0.68 (s, 2H), 0.59 (d, 3H, minor diastereomer), 0.28 (d, 3H, major diastereomer).

後処理

  1. customTo a 50-mL round-bottom flask equipped with a magnetic stirbar
  2. customthe reaction mixture was capped with a rubber septum
  3. customThe sodium chloride side product was remove by gravity filtration
  4. concentrationthe filtrate was concentrated on a rotary evaporator
  5. customThe crude oily product was purified by flash chromatography
  6. washeluting with hexanes

出典と根拠

ORDレコード
ord-0a286e3ff5b548f5ad46e9563e234492
出典データセット
uspto-grants-2014_09
特許番号
US08821922B2

反応ノート

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