Methyl Acrylate → HCID 89851376、化合物

HRID 627262

反応式

HRID 627262 の反応式
[CH3:1][O:2][CH2:3][C@@H:4]([N:7]([CH2:15][CH:16]=[O:17])[C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH:5]=[CH2:6].[C:18]([O:22][CH3:23])(=[O:21])[CH:19]=[CH2:20].N12CCC(CC1)CC2>CO>[C:10]([O:9][C:8]([N:7]([C@@H:4]([CH:5]=[CH2:6])[CH2:3][O:2][CH3:1])[CH2:15][CH:16]([OH:17])[C:19](=[CH2:20])[C:18]([O:22][CH3:23])=[O:21])=[O:14])([CH3:12])([CH3:13])[CH3:11]

参加物

5

反応物 3

HCID 7294Methyl AcrylateHCID 7527Quinuclidine2 回HCID 89863093HCID 89863093、化合物2 回

生成物 1

HCID 89851376HCID 89851376、化合物収率 65%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of (S)-tert-butyl 1-methoxybut-3-en-2-yl(2-oxoethyl)carbamate (Intermediate 252, 1.475 g, 6.06 mmol) and methyl acrylate (0.82 ml, 9.09 mmol) in MeOH (0.2 ml) under nitrogen at room temperature was added quinuclidine (0.337 g, 3.03 mmol). The reaction mixture was stirred at that temperature overnight. Another 100 mg of quinuclidine was added and the reaction was stirred for another 24 hours. The reaction mixture was then partitioned between water and ethyl acetate. The layers were separated and the organics were washed with water and brine, then dried over magnesium sulfate, filtered and concentrated. Silica gel chromatography (0%-30% ethyl acetate/hexanes) afforded the title compound as a clear oil (1.28 g, 65%). The product is a mixture of two diastereomers.

後処理

  1. stirringthe reaction was stirred for another 24 hours
  2. customThe reaction mixture was then partitioned between water and ethyl acetate
  3. customThe layers were separated
  4. washthe organics were washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-e080e644243f4d5097cb3905e31e5222
出典データセット
uspto-grants-2016_04
特許番号
US09309245B2

関連ノート

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