Methanamine, N-methoxy-, hydrochloride (1:1) → N,3,3-Trimethoxy-N-methylcyclobutanecarboxamide

HRID 1778564ノート

反応式

HRID 1778564 の反応式
[CH3:1][O:2][C:3]1([O:11][CH3:12])[CH2:6][CH:5]([C:7]([O:9]C)=O)[CH2:4]1.Cl.[CH3:14][NH:15][O:16][CH3:17].C([Mg]Cl)(C)C>C1COCC1>[CH3:17][O:16][N:15]([CH3:14])[C:7]([CH:5]1[CH2:4][C:3]([O:2][CH3:1])([O:11][CH3:12])[CH2:6]1)=[O:9]

参加物

5

反応物 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 10487446Methyl 3,3-dimethoxycyclobutane-1-carboxylateHCID 178418918HCID 178418918、化合物

生成物 1

HCID 86624599N,3,3-Trimethoxy-N-methylcyclobutanecarboxamide収率 67.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Methyl 3,3-dimethoxycyclobutanecarboxylate (11.65 g, 66.9 mmol) was dissolved in THF (134 mL) and treated with N,O-dimethylhydroxylamine hydrochloride (10.12 g, 103.7 mmol). The mixture was cooled to 0° C. and treated with isopropylmagnesium chloride (2 M solution in THF, 100.3 mL, 200.7 mmol) and stirred for 2 h. The reaction was quenched with saturated ammonium chloride solution (75 mL), diluted with ethyl acetate, washed with water and saturated aqueous sodium chloride, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 20-100% ethyl acetate in heptane to afford the desired product (9.16 g, 67%). Rf 0.06 (20% ethyl acetate in heptane). 1H NMR (CDCl3, 300 MHz) δ 3.61 (s, 3H), 3.20 (s, 3H), 3.19 (s, 3H), 3.15 (s, 3H), 2.39 (d, J=9.0 Hz, 4H). ESI MS found for C9H17NO4 m/z [204.1 (M+1)].

後処理

  1. customThe reaction was quenched with saturated ammonium chloride solution (75 mL)
  2. additiondiluted with ethyl acetate
  3. washwashed with water and saturated aqueous sodium chloride
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel eluting with 20-100% ethyl acetate in heptane

出典と根拠

ORDレコード
ord-85db88f9a5dc475795c03306aea2b22a
出典データセット
uspto-grants-2016_02
特許番号
US09266908B2

反応ノート

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