Water → 7-Bromo-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid methyl ester

HRID 467559ノート

反応式

HRID 467559 の反応式
Cl[C:2]([O:4][CH3:5])=[O:3].[Br:6][C:7]1[CH:17]=[CH:16][C:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15][C:9]=2[CH:8]=1.C(N(CC)CC)C.O>ClCCl>[CH3:5][O:4][C:2]([N:13]1[CH2:14][CH2:15][C:9]2[CH:8]=[C:7]([Br:6])[CH:17]=[CH:16][C:10]=2[CH2:11][CH2:12]1)=[O:3]

参加物

6

反応物 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 468400337-Bromo-2,3,4,5-tetrahydro-1H-3-benzazepine

生成物 1

HCID 674693277-Bromo-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid methyl ester収率 98.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Methyl chloroformate (444 mg, 4.70 mmol) was added to a 0° C. mixture of 7-bromo-2,3,4,5-tetrahydro-1H-benzo[d]azepine (950 mg, 3.82 mmol) and triethylamine (915 mg, 9.04 mmol) in 19 mL of dichloromethane. The resulting solution was stirred at 0° C. for 2 h. Water was added, the layers were separated and the aqueous phase was washed with dichloromethane, and the combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated to leave 1.07 g of an oil. This material was combined with 52 mg from an earlier experiment and purified by column chromatography on silica gel (24 g SiO2, Analogix column) eluting @ 30 mL/min with 1:1 ethyl acetate/heptane. 763 mg of product was obtained.

後処理

  1. customthe layers were separated
  2. washthe aqueous phase was washed with dichloromethane
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-76f6df8389c44d94b299783fa7ce58e8
出典データセット
uspto-grants-2014_01
特許番号
US08623877B2

反応ノート

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