Methyl Acrylate → HCID 89851376, 화합물

HRID 627262

반응식

HRID 627262 반응식
[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]

참가 물질

5

반응물 3

HCID 7294Methyl AcrylateHCID 7527Quinuclidine2회HCID 89863093HCID 89863093, 화합물2회

생성물 1

HCID 89851376HCID 89851376, 화합물수율 65%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e080e644243f4d5097cb3905e31e5222
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309245B2

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