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Trimethylsilyl iodide → Methyl(5r)-5-propynyl-l-prolinate

HRID 475400
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HRID 475400 반응식
[C:1]([C@@H:4]1[N:8](C(OC)=O)[C@H:7]([C:13]([O:15][CH3:16])=[O:14])[CH2:6][CH2:5]1)#[C:2][CH3:3].I[Si](C)(C)C>C(Cl)(Cl)Cl>[C:1]([C@@H:4]1[NH:8][C@H:7]([C:13]([O:15][CH3:16])=[O:14])[CH2:6][CH2:5]1)#[C:2][CH3:3]
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참가 물질

4

반응물 2

HCID 85247Trimethylsilyl iodideHCID 66756906dimethyl(2S,5R)-5-propynyl-pyrrolidine-1,2-dicarboxylate

생성물 1

HCID 16090848Methyl(5r)-5-propynyl-l-prolinate

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

A solution of dimethyl(2S,5R)-5-propynyl-pyrrolidine-1,2-dicarboxylate (4.25 g, 18.90 mmol) and iodotrimethylsilane (3.23 mL, 22.7 mmol, Example 85A) in chloroform (60 mL) was heated to 65° C. for 3 hours, was cooled to room temperature, concentrated under reduced pressure and flash chromatographed with 35% ethyl acetate/65% hexane to provide the titled compound. MS (DCI/NH3) m/e 168 (M+H)+.

후처리

  1. concentrationconcentrated under reduced pressure and flash
  2. customchromatographed with 35% ethyl acetate/65% hexane

출처 및 근거

ORD 기록
ord-2c1e9e53d9db4afbb25ed331652a2217
출처 데이터셋
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08637546B2

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