Propargyl bromide → 3-(Benzhydrylidene-amino)-1-methyl-3-prop-2-ynyl-pyrrolidin-2-one

HRID 2207685노트

반응식

HRID 2207685 반응식
[CH3:1][C:2](C)([O-])[CH3:3].[K+].[C:7](=[N:20][CH:21]1[CH2:25][CH2:24][N:23]([CH3:26])[C:22]1=[O:27])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(Br)C#C>C1COCC1.CC(O)C>[C:7](=[N:20][C:21]1([CH2:3][C:2]#[CH:1])[CH2:25][CH2:24][N:23]([CH3:26])[C:22]1=[O:27])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

참가 물질

6

반응물 3

HCID 7842Propargyl bromideHCID 23665647Potassium tert-butoxide2회HCID 896489983-(Benzhydrylidene-amino)-1-methyl-pyrrolidin-2-one

생성물 1

HCID 896495353-(Benzhydrylidene-amino)-1-methyl-3-prop-2-ynyl-pyrrolidin-2-one

시약·촉매·용매 2

HCID 3776Isopropanol용매HCID 8028Tetrahydrofuran용매2회

실험 절차

Potassium tert-butoxide 1.7M in THF (32.8 mL, 55.76 mmol) was added dropwise over a period of 80 minutes (by syringe pump) to a solution of the 3-(benzhydrylidene-amino)-1-methyl-pyrrolidin-2-one (14.11 g, 50.692 mmol) (which may be prepared as described in Description 1) and propargyl bromide (6.78 mL, 60.83 mmol) in THF (250 mL) at 0° C. under nitrogen. The reaction was stirred for 2 hours. Additional KOtBu (5 ml) was added dropwise and stirring was continued for 15 mins. The reaction was quenched by the addition of satd. aq. NaHCO3 and diluted with EtOAc. The phases were separated, the organic layer was dried (Na2SO4) and the solvent evaporated to afford a crude brown oil which solidified on standing. This waxy-solid was suspended in IPA (approx. 30 ml) and stirred for 1 hr. The solid was filtered off, washed with a little IPA to afford 3-(benzhydrylidene-amino)-1-methyl-3-prop-2-ynyl-pyrrolidin-2-one (D2) as a light brown solid (6.26 g);

후처리

  1. stirringstirring
  2. waitwas continued for 15 mins
  3. customThe reaction was quenched by the addition of satd
  4. additionaq. NaHCO3 and diluted with EtOAc
  5. customThe phases were separated
  6. dry with materialthe organic layer was dried (Na2SO4)
  7. customthe solvent evaporated
  8. customto afford a crude brown oil which
  9. stirringstirred for 1 hr
  10. filtrationThe solid was filtered off
  11. washwashed with a little IPA

출처 및 근거

ORD 기록
ord-6ebfd8c8a9084b0c83e611941aacfd55
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09376445B2

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