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

HRID 1778564노트

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HRID 1778564 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 86624599N,3,3-Trimethoxy-N-methylcyclobutanecarboxamide수율 67.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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)].

후처리

  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

출처 및 근거

ORD 기록
ord-85db88f9a5dc475795c03306aea2b22a
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266908B2

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