1,4-Dibromobutane → 3-(4-Bromobutyl)-1-(phenylmethyl)-2-pyrrolidinone

HRID 1097728

반응식

HRID 1097728 반응식
[C:1]1([CH2:7][N:8]2[CH2:12][CH2:11][CH2:10][C:9]2=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:14][CH2:15][CH2:16][CH2:17][CH2:18]Br.C1(CN2CCC3(CCCC3)C2=O)C=CC=CC=1>C1COCC1>[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:10]1[CH2:11][CH2:12][N:8]([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:9]1=[O:13]

참가 물질

5

반응물 3

HCID 80561,4-DibromobutaneHCID 791761-Benzyl-3-pyrrolidoneHCID 157074382-(Phenylmethyl)-2-azaspiro[4.4]nonan-1-one

생성물 1

HCID 593958573-(4-Bromobutyl)-1-(phenylmethyl)-2-pyrrolidinone

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 1-(phenylmethyl)-2-pyrrolidinone (0.47 g, 2.7 mmol) in THF (10 ml) at −78° C. was added lithium hexamethyldisilylazine (2.8 ml, 2.7 mmol, 1M solution) over 5 min. After 15 min 1,4-dibromobutane (0.32 ml, 2.7 mmol) was added and the solution allowed to attain ambient temperature over 2 h then stirred for a further 18 h. The solution was separated between ethyl acetate and water and the organics isolated, dried and concentrated. Chromatography over silica (20 g SPE) eluting with cyclohexane then DCM and finally ether provided a clear oil which was a 1:1 mixture of the title compound and 2-(phenylmethyl)-2-azaspiro[4.4]nonan-1-one (0.17 g). This was used in the next step without further purification.

후처리

  1. customThe solution was separated between ethyl acetate and water
  2. customthe organics isolated, dried
  3. concentrationconcentrated
  4. washChromatography over silica (20 g SPE) eluting with cyclohexane
  5. customDCM and finally ether provided a clear oil which

출처 및 근거

ORD 기록
ord-d7f2e482a58640648abc361619115a0f
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143264B2

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