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Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine → Benzyl (3RS,4SR)-1-benzyl-4-methylpyrrolidine-3-carboxylate

HRID 445992
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HRID 445992 반응식
[C:1]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:5])/[CH:2]=[CH:3]/[CH3:4].CO[CH2:16][N:17]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:18][Si](C)(C)C>ClCCl.FC(F)(F)C(O)=O>[CH2:23]([N:17]1[CH2:16][CH:3]([CH3:4])[CH:2]([C:1]([O:6][CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[O:5])[CH2:18]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 5356259Benzyl crotonate, (E)-

생성물 1

HCID 86678243Benzyl (3RS,4SR)-1-benzyl-4-methylpyrrolidine-3-carboxylate수율 105.9%

시약·촉매·용매 2

HCID 6422Trifluoroacetic acid촉매HCID 6344Dichloromethane용매

실험 절차

Benzyl (2E)-but-2-enoate obtained in Example 1e (20.5 g, 116 mmol) was dissolved in dichloromethane (5 ml), and the mixture was cooled in an ice bath with stirring. Trifluoroacetic acid (257 μl, 3.47 mmol) was added, and N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (33.1 g, 139 mmol) was added dropwise to the reaction liquid over 15 minutes so that the internal temperature did not exceed 62° C., while washing with dichloromethane (25 ml). The reaction liquid was left to stand until it reached mom temperature and was stirred for 15 hours. The reaction liquid was concentrated and purified by silica gel column chromatography (elution solvent: ethyl acetate/heptane) to give the title compound (38 g).

후처리

  1. temperaturethe mixture was cooled in an ice bath
  2. customdid not exceed 62° C.
  3. washwhile washing with dichloromethane (25 ml)
  4. customThe reaction liquid
  5. waitwas left
  6. stirringwas stirred for 15 hours
  7. customThe reaction liquid
  8. concentrationwas concentrated
  9. custompurified by silica gel column chromatography (elution solvent: ethyl acetate/heptane)

출처 및 근거

ORD 기록
ord-da6d19fbe0344d7b839b55a9cac26898
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08476301B2

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