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

HRID 1275486ノート

反応式

HRID 1275486 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 12344035(R)-5-Phenylpyrrolidin-2-one収率 98%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
55 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-16a1275be0654ee8bd78f1d40fe4bb8a
出典データセット
uspto-grants-2000_12
特許番号
US06162417

反応ノート

読み込み中…