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

Magnesium → (2S,4R)-2-methyl 1-(2-(trimethylsilyl)ethyl) 4-(5'-chloro-2'-vinylbiphenyl-4-yl)-4-hydroxypyrrolidine-1,2-dicarboxylate

HRID 1043426
노트
인쇄 미리보기

반응식

HRID 1043426 반응식
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=2[CH:16]=[CH2:17])=[CH:5][CH:4]=1.[O:18]=[C:19]1[CH2:23][N:22]([C:24]([O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])=[O:25])[C@H:21]([C:33]([O:35][CH3:36])=[O:34])[CH2:20]1>C1COCC1.C(Cl)Cl>[Cl:15][C:13]1[CH:12]=[CH:11][C:10]([CH:16]=[CH2:17])=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([C@@:19]3([OH:18])[CH2:23][N:22]([C:24]([O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:30])[CH3:31])=[O:25])[C@H:21]([C:33]([O:35][CH3:36])=[O:34])[CH2:20]3)=[CH:4][CH:5]=2)[CH:14]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 5462224Magnesium3회HCID 59266363(S)-2-methyl 1-(2-(trimethylsilyl)ethyl) 4-oxopyrrolidine-1,2-dicarboxylateHCID 592665224'-Bromo-5-chloro-2-vinylbiphenyl

생성물 1

HCID 59266523(2S,4R)-2-methyl 1-(2-(trimethylsilyl)ethyl) 4-(5'-chloro-2'-vinylbiphenyl-4-yl)-4-hydroxypyrrolidine-1,2-dicarboxylate수율 14%

시약·촉매·용매 2

HCID 6344
Dichloromethane
용매
HCID 8028Tetrahydrofuran용매2회

실험 절차

Magnesium (0.298 g, 12.27 mmol) was stirred in a round bottom flask under nitrogen for 15 min. to cause scratching of the surface of the magnesium turnings. 10 mL of THF was added to the magnesium turnings and stirred for an additional 30 min. 4′-bromo-5-chloro-2-vinylbiphenyl (3.43 g, 11.68 mmol) in THF (60 mL), was added in dropwise at reflux with vigorous stirring. The Grignard solution was added to a solution of (S)-2-methyl 1-(2-(trimethylsilyl)ethyl) 4-oxopyrrolidine-1,2-dicarboxylate (3.35 g, 11.67 mmol) in DCM (60 mL) at r.t. and stirred for 1 hr and then quenched with saturated NH4Cl solution. The aqueous layer was extracted with DCM and the combined organics were dried, filtered and evaporated to give crude material. The crude material was purified by flash chromatography on the Biotage (10-40% EtOAc:Hex) to give (2S,4R)-2-methyl 1-(2-(trimethylsilyl)ethyl) 4-(5′-chloro-2′-vinylbiphenyl-4-yl)-4-hydroxypyrrolidine-1,2-dicarboxylate (800 mg, 1.593 mmol, 14% yield) as a yellow oil. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 0.04 (s, 9H) 1.03 (dd, j=9.46, 7.63 Hz, 2H) 2.30-2.48 (m, 1H) 2.63-2.79 (m, 1H) 3.77-3.80 (m, 1H) 3.82-3.86 (m, 3H) 3.95-4.05 (m, 1H) 4.16-4.26 (m, 2H) 4.51-4.67 (m, 1H) 5.20 (d, J=11.90 Hz, 1H) 5.67 (d, J=17.40 Hz, 1H) 6.61 (dd, J=17.40, 10.99 Hz, 1H) 7.26-7.35 (m, 4H) 7.49-7.58 (m, 3H).

후처리

  1. temperatureat reflux with vigorous stirring
  2. stirringstirred for 1 hr
  3. customquenched with saturated NH4Cl solution
  4. extractionThe aqueous layer was extracted with DCM
  5. customthe combined organics were dried
  6. filtrationfiltered
  7. customevaporated
  8. customto give crude material
  9. customThe crude material was purified by flash chromatography on the Biotage (10-40% EtOAc:Hex)

출처 및 근거

ORD 기록
ord-65d2ee8843f744c3aafd2735a2002595
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08563505B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트