Sodium Cyanide → (R)-5-Phenylpyrrolidin-2-one

HRID 1275486노트

반응식

HRID 1275486 반응식
[NH2:1][C@@H:2]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:3][CH2:4][C:5](OCC)=[O:6].[C-]#N.[Na+]>CO>[C:10]1([C@@H:2]2[NH:1][C:5](=[O:6])[CH2:4][CH2:3]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

참가 물질

4

반응물 2

HCID 8929Sodium CyanideHCID 20638623ethyl 4(R)-amino-4-phenylbutyrate

생성물 1

HCID 12344035(R)-5-Phenylpyrrolidin-2-one수율 98%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
55 °C

실험 절차

To a stirred solution of ethyl 4(R)-amino-4-phenylbutyrate (515 mg, 2.48 mmol) in 20 mL of anhydrous methanol was added sodium cyanide (25 mg, 0.5 mmol) at room temperature. The reaction mixture was stirred at 55° C. for 4 h, cooled to room temperature, concentrated under reduced pressure. The residue was taken up in methylene chloride, washed with water, brine, dried over anhydrous MgSO4, concentrated to afford 391 mg of product (98% yield) as a colorless crystal, mp 103-105° C. (lit.17 102-104° C.). 1H NMR (CDCl3) δ 1.80-1.95 (m, 1H), 2.27-2.42 (m, 2H), 2.45-2.58 (m, 1H), 4.709 (t, 1H, J=7.2 Hz), 7.22-7.38 (m, 5H), 7.425 (br, 1H); 13C NMR (CDCl3) δ 30.19, 30.93, 57.91, 125.34, 127.46, 128.56, 142.43, 178.85.

후처리

  1. temperaturecooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. washwashed with water, brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-16a1275be0654ee8bd78f1d40fe4bb8a
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06162417

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