홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Trifluoroacetic acid → (+/-)-trans-Benzyl 1-benzyl-4-(2-(methoxycarbonyl)-3-(trifluoromethyl)phenyl)pyrrolidine-3-carboxylate

HRID 2100576
노트
인쇄 미리보기

반응식

HRID 2100576 반응식
[CH2:1]([O:8][C:9](=[O:26])/[CH:10]=[CH:11]/[C:12]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[C:13]=1[C:14]([O:16][CH3:17])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[CH2:29][N:30]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:31][Si](C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl.CCOC(C)=O.COCN(CC1C=CC=CC=1)C[Si](C)(C)C.FC(F)(F)C(O)=O>[CH2:36]([N:30]1[CH2:31][C@@H:11]([C:12]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:24])([F:25])[F:23])[C:13]=2[C:14]([O:16][CH3:17])=[O:15])[C@H:10]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:26])[CH2:29]1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 69055523HCID 69055523, 화합물

생성물 1

HCID 131727567(+/-)-trans-Benzyl 1-benzyl-4-(2-(methoxycarbonyl)-3-(trifluoromethyl)phenyl)pyrrolidine-3-carboxylate수율 95.5%

시약·촉매·용매 4

HCID 6422Trifluoroacetic acid
촉매
HCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine촉매
HCID 6344Dichloromethane용매
HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (E)-methyl 2-(3-(benzyloxy)-3-oxoprop-1-enyl)-6-(trifluoromethyl)benzoate (5.83 g, 16.0 mmol) in 60 mL of CH2Cl2 was added N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (4.0 g, 16.8 mmol) and trifluoroacetic acid (0.25 mL, 3.2 mmol). The solution was allowed to stir at ambient temperature for 18 h. Starting material still remained by TLC analysis and so additional N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (0.25 g, 1.05 mmol) and trifluoroacetic acid (0.05 mL, 0.65 mmol) were added and the reaction was stirred at 40° C. for an additional 2 h. The reaction was allowed to cool and was diluted with EtOAc, washed with sat'd aq NaHCO3 and brine, dried (MgSO4) and concentrated. The residue was purified by flash chromatography (4:1 hexane/EtOAc) to afford 7.6 g (95%) of the title compound as an oil. LRMS (ES)+: 498.32 (M+H)+.

후처리

  1. additionwere added
  2. stirringthe reaction was stirred at 40° C. for an additional 2 h
  3. temperatureto cool
  4. washwashed with sat'd aq NaHCO3 and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (4:1 hexane/EtOAc)

출처 및 근거

ORD 기록
ord-bce74ba8d2fb4184860671c4bcc09dd2
출처 데이터셋
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07572805B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트