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

HRID 20623

反応式

HRID 20623 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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)+.

後処理

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

出典と根拠

ORDレコード
ord-c20dc84ed9674e7a8af065a7979aa4ca
出典データセット
uspto-grants-2010_06
特許番号
US07745665B2

関連ノート

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