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

HRID 626875Notes

Reaction equation

HRID 626875 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

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);

Workup

  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

Sources & evidence

ORD record
ord-ac73da3e3cc04e55abf1ee7e854846f6
Source dataset
uspto-grants-2016_04
Patent number
US09309254B2

Reaction notes

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