Propargyl bromide → HCID 15086767, compound

HRID 2107977Notes

Reaction equation

HRID 2107977 reaction equation
[CH3:1][C:2]([Si:5]([CH3:14])([CH3:13])[O:6][C@H:7]1[CH2:11][CH2:10][NH:9][C:8]1=[O:12])([CH3:4])[CH3:3].[H-].[Na+].[CH2:17](Br)[C:18]#[CH:19]>O1CCCC1.C1(C)C=CC=CC=1.ClCCl>[CH3:4][C:2]([Si:5]([CH3:14])([CH3:13])[O:6][C@H:7]1[CH2:11][CH2:10][N:9]([CH2:19][C:18]#[CH:17])[C:8]1=[O:12])([CH3:1])[CH3:3]

Participants

7

Reactant 3

HCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 10584804(S)-3-((tert-Butyldimethylsilyl)oxy)pyrrolidin-2-one

Product 1

HCID 15086767HCID 15086767, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In one portion, 11.6 g of (S)-3-[[(1,1-dimethyl-ethyl)dimethylsilyl]oxy]-2-pyrrolidinone was added to a suspension of 2.35 g of 60% sodium hydride in mineral oil in 400 ml of tetrahydrofuran which was cooled to 0° C. The resulting solution was stirred at room temperature until solution was complete, then recooled to 0° C. An 80% solution of propargyl bromide in toluene (8.5 ml) was added and the resulting solution was stirred overnight. The solution was diluted with dichloromethane, washed with water, dried and concentrated in vacuo. The residue was purified by chromatography (silica gel), giving (S)-3-[[(1,1-dimethylethyl)-dimethylsilyl]oxy]-1-(2-propynyl)-2-pyrrolidinone, [α]D26 =-44° (dichloromethane); mp 35°-36° C.

Workup

  1. customrecooled to 0° C
  2. stirringthe resulting solution was stirred overnight
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography (silica gel)

Sources & evidence

ORD record
ord-1c7552f00aef4e47ae26660cce285550
Source dataset
uspto-grants-1990_06
Patent number
US04937235

Reaction notes

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