(R)-beta-aminophenethyl alcohol → HCID 90025824, 화합물

HRID 59690

반응식

HRID 59690 반응식
[CH3:1][CH:2]([CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:3]([O:5]N1C(=O)CCC1=O)=O.[CH:22]1[CH:27]=[CH:26][C:25]([C@@H:28]([NH2:31])[CH2:29][OH:30])=[CH:24][CH:23]=1>C1COCC1>[OH:30][CH2:29][C@H:28]([NH:31][C:3](=[O:5])[C@@H:2]([CH3:1])[CH2:13][CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:25]1[CH:26]=[CH:27][CH:22]=[CH:23][CH:24]=1

참가 물질

4

반응물 2

HCID 2724025(R)-beta-aminophenethyl alcoholHCID 90026070HCID 90026070, 화합물

생성물 1

HCID 90025824HCID 90025824, 화합물수율 34%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
48 °C

실험 절차

To a solution consisting of (±)-2,5-dioxopyrrolidin-1-yl 2-methyl-5-phenyl pentanoate (18mb(i), 85.6 g, 296 mmol) in THF (3000 mL) at 48° C. was added R-(−)-2-phenylglycinol (65.9 g, 480 mmol, Bridge Organics) in portions. The resulting reaction mixture was stirred at 48° C. for 40 hours. A white precipitate formed, which was filtered from the reaction mixture and washed with THF. The filtrate was concentrated under vacuum and the residue, comprising the diastereomeric pair, was chromatographed on silica gel. Elution with ethyl acetate-heptane (50:50 v/v) afforded the pure diastereomer title compound (31.3 g, 34%) as a colorless solid; TLC Rf 0.205 (solvent system: 50:50 v/v ethyl acetate-heptane); HPLC retention time 15.1 minutes, stationary phase: Gemini 5μ C18 250×4.6 mm, ultraviolet detector at 210 nm, mobile phase: 1 mL/min, 60:40:0.1 v/v methanol-water-acetic acid.

후처리

  1. customThe resulting reaction mixture
  2. customA white precipitate formed
  3. filtrationwhich was filtered from the reaction mixture
  4. washwashed with THF
  5. concentrationThe filtrate was concentrated under vacuum
  6. customwas chromatographed on silica gel
  7. washElution with ethyl acetate-heptane (50:50 v/v)

출처 및 근거

ORD 기록
ord-845b5e6a71054bcaa8d4933eb583801c
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440919B2

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