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

HRID 626875ノート

反応式

HRID 626875 の反応式
[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

参加物

6

反応物 3

HCID 7842Propargyl bromideHCID 23665647Potassium tert-butoxide2 回HCID 896489983-(Benzhydrylidene-amino)-1-methyl-pyrrolidin-2-one

生成物 1

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

試薬・触媒・溶媒 2

HCID 3776Isopropanol溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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);

後処理

  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

出典と根拠

ORDレコード
ord-ac73da3e3cc04e55abf1ee7e854846f6
出典データセット
uspto-grants-2016_04
特許番号
US09309254B2

反応ノート

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