Allyl bromide → HCID 19705440, compound

HRID 727543Notes

Reaction equation

HRID 727543 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:21][CH:22]([CH3:24])[CH3:23])([CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:9]1=[O:25])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[CH3:27][CH:28]([N-]C(C)C)[CH3:29].C(Br)C=C>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:21][CH:22]([CH3:23])[CH3:24])([CH:13]([C:28]([CH3:29])=[CH2:27])[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:9]1=[O:25])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 2724682Lithium diisopropylamideHCID 53993409HCID 53993409, compound

Product 1

HCID 19705440HCID 19705440, compoundYield 115.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of tert-butyl N-tert-butyloxycarbonyl-3-(2-methylpropyl)-2-oxo-3-pyrrolidineacetate (3.65 g, 10.3 mmol) in dry THF (45 mL) is cooled to -78° C. and treated drop-wise with LDA (5.70 mL, 11.3 mmol). After 30 minutes at -78° C., allyl bromide (1.10 mL, 12.4 mmol) is added. The solution is maintained at -78° C. for 3 hours, and is then allowed to slowly warm to room temperature under N2. After 12 hours, the solution is quenched with saturated NH4Cl (10 mL) and diluted with H2O (50 mL). The crude lactem is extracted into EtOAc (3×100 mL). The organic extracts are combined, washed with brine (50 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to give 4.72 g of gold oil. The oil is purified by silica gel chromatography (300 g SG, 5% EtOAc/hexane) to yield 2.98 g (73%) of the title compound as a clear, pale gold oil as a mixture of diastereomers.

Workup

  1. temperatureto slowly warm to room temperature under N2
  2. waitAfter 12 hours
  3. customthe solution is quenched with saturated NH4Cl (10 mL)
  4. additiondiluted with H2O (50 mL)
  5. extractionThe crude lactem is extracted into EtOAc (3×100 mL)
  6. washwashed with brine (50 mL)
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6dae4e253d3242d2acda8a935dc08c95
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

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