Ethanolamine → 1-(2-Hydroxyethyl)-3,3-diphenylpyrrolidin-2-one

HRID 1667133

반응식

HRID 1667133 반응식
[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][CH2:10][O:9][C:8]2=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:19][CH2:20][CH2:21][OH:22]>[Cl-].[Zn+2].[Cl-]>[OH:22][CH2:21][CH2:20][N:19]1[CH2:10][CH2:11][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8]1=[O:9]

참가 물질

4

반응물 2

HCID 700EthanolamineHCID 70393Dihydro-3,3-diphenyl-2(3H)-furanone

생성물 1

HCID 673575371-(2-Hydroxyethyl)-3,3-diphenylpyrrolidin-2-one

시약·촉매·용매 1

HCID 3007855Zincchloride촉매

반응 조건

온도
100 °C

실험 절차

A mixture of 3,3-diphenyldihydrofuran-2(3H)-one (0.5 g, 2.098 mmol), 2-aminoethanol (1282 mg, 20.98 mmol) and zinc chloride (0.23 g, 1.679 mmol) was heated neat at 100° C. for 16 hours. The reaction mixture was cooled and partitioned in H2O/ethyl acetate. The organic layer was separated, dried over MgSO4, and concentrated to yield the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 7.32 (m, 8H), 7.23 (m, 2H), 3.81 (q, J=5.42 Hz, 2H), 3.52 (t, J=5.42 Hz, 2H), 3.45 (t, J=6.44 Hz, 2H), 2.85 (t, J=5.52 Hz, 1H), 2.79 (t, J=6.44 Hz, 2H); MS (ESI+) m/z 282 (M+H)+.

후처리

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned in H2O/ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ac44c9d704d04ff297f65de067ef0708
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044069B2

연결된 노트

불러오는 중…