Sodium Iodide → HCID 86625664, 화합물

HRID 68199노트

반응식

HRID 68199 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 86625664HCID 86625664, 화합물

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0a286e3ff5b548f5ad46e9563e234492
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08821922B2

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