Methyl chloroformate → methyl N-[2-(3-methoxyphenyl)ethyl]carbamate

HRID 130933

反応式

HRID 130933 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH2:11])[CH:6]=[CH:7][CH:8]=1.C1COCC1.CCN(CC)CC.Cl[C:25]([O:27][CH3:28])=[O:26]>C(OCC)(=O)C.O>[CH3:28][O:27][C:25](=[O:26])[NH:11][CH2:10][CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1

参加物

7

反応物 4

HCID 6586Methyl chloroformateHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 748663-Methoxyphenethylamine

生成物 1

HCID 13948245methyl N-[2-(3-methoxyphenyl)ethyl]carbamate収率 98.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Combine 2-(3-methoxyphenyl)ethylamine (9.6 mL, 66.1 mmol), THF (300 mL), Et3N (11.0 mL, 78.9 mmol), and methyl chloroformate (26.0 mL, 339 mmol) at 0° C. under nitrogen atmosphere. Stir at room temperature for 18 hours, add the mixture into water, wash with brine, and dry the organic layer over Na2SO4 followed by concentrating under reduced pressure. Flash chromatograph using 2:1 hexanes:ethyl acetate to afford 13.6 g, 65.0 mmol (98% yield) of the title compound: 1H NMR (500 MHz, CDCl3); 2.8 (2H, t, J=6.7, 7.0 Hz), 3.41-3.46 (2H, m), 3.7 (3H, s), 3.8 (3H, s), 4.6-4.8 (1H, br s), 6.7-6.8 (3H, m), 7.2-7.3 (1H, m); MS m/z 210 (M+1).

後処理

  1. customat 0° C.
  2. washwash with brine
  3. dry with materialdry the organic layer over Na2SO4
  4. concentrationby concentrating under reduced pressure

出典と根拠

ORDレコード
ord-f81172751efa451e99472a47d0f49f54
出典データセット
uspto-grants-2008_06
特許番号
US07381719B2

関連ノート

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