Ethyl Acetate → 1-(3-Methoxymethoxy-phenyl)-2-methylamino-ethanol

HRID 20623

반응식

HRID 20623 반응식
Cl.CN.[CH:4]([N:7](C(C)C)CC)(C)C.[CH3:13][O:14][CH2:15][O:16][C:17]1[CH:18]=[C:19]([CH:23]2[CH2:25][O:24]2)[CH:20]=[CH:21][CH:22]=1.C(OCC)(=O)C>CO>[CH3:13][O:14][CH2:15][O:16][C:17]1[CH:18]=[C:19]([CH:23]([OH:24])[CH2:25][NH:7][CH3:4])[CH:20]=[CH:21][CH:22]=1

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 6364545Methylamine hydrochlorideHCID 167536502-(3-Methoxymethoxy-phenyl)-oxirane

생성물 1

HCID 593480531-(3-Methoxymethoxy-phenyl)-2-methylamino-ethanol수율 20%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Methylamine hydrochloride (275 mg, 4.08 mmol) and diisopropylethylamine (601 mg, 4.66 mmol) were sequentially added to a solution of 2-(3-methoxymethoxy-phenyl)-oxirane (210 mg, 1.16 mmol) in anhydrous methanol (5 mL). The resulting mixture was maintained at ambient temperature for about 12 hours. Following standard extractive workup with ethyl acetate, the crude product was purified by flash column chromatography on silica gel (1×15 cm, dichloromethane/methanol/NH4OH=90/8/1 elution) to give the title product (49 mg, 20%). 1H NMR (300 MHz, CDCl3) δ 7.26-7.23 (m, 1H), 7.06 (s, 1H), 7.00 (d, 1H, J=7.5 Hz), 6.95 (d, 1H, J=6.9 Hz), 5.18 (s, 2H), 4.71 (d, 1H, J=5.7 Hz), 3.48 (s, 3H), 2.84-2.62 (m, 2H), 2.46 (s, 3H); LC-MS: m/z=212 (MH)+.

후처리

  1. customthe crude product was purified by flash column chromatography on silica gel (1×15 cm, dichloromethane/methanol/NH4OH=90/8/1 elution)

출처 및 근거

ORD 기록
ord-c20dc84ed9674e7a8af065a7979aa4ca
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745665B2

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