Allyl bromide → HCID 69898152, compound

HRID 496248Notes

Reaction equation

HRID 496248 reaction equation
[C:1]([N:8]1[CH2:16][C:15](=[O:17])[CH2:14][C@H:9]1[C:10]([O:12][CH3:13])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:18](Br)[CH:19]=[CH2:20].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH2:32]1[CH2:36]OC[CH2:33]1>CN1C(=O)N(C)CCC1>[C:1]([N:8]1[CH2:16][C:15](=[O:17])[C:14]([CH2:36][CH:32]=[CH2:33])([CH2:18][CH:19]=[CH2:20])[C@H:9]1[C:10]([O:12][CH3:13])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 8028TetrahydrofuranHCID 2733832Lithium HexamethyldisilazideHCID 109884851-tert-butyl 2-methyl (2S)-4-oxopyrrolidine-1,2-dicarboxylate

Product 1

HCID 69898152HCID 69898152, compound

Reagents, catalysts & solvents 1

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Conditions

Temperature
-78 °C

Procedure

To a solution of N-(BOC)-4-oxo-(L)-proline, methyl ester (0.197 g) in 3 mL of THF and 1 mL of DMPU was added 0.28 mL of allyl bromide. The reaction mixture was cooled to −78° C. and 2.0 mL of LiHMDS was dropwise introduced into the reaction. The mixture was stirred at −78° C. for 2 h and then was allowed to warm to rt and stirred under nitrogen overnight. The reaction was quenched with saturated NH4Cl and diluted with water. The mixture was extracted with Et2O (3×). The combined Et2O layers were washed with water, brine and dried over anhydrous Na2SO4. After concentration in vacuo, the crude product was purified by flash column chomatography on silica gel eluted with 5%-10% EtOAc/Hexane to isolate 0.099 g of N-(BOC)-3,3-diallyl-4-oxoproline, methyl ester.

Workup

  1. temperatureto warm to rt
  2. stirringstirred under nitrogen overnight
  3. customThe reaction was quenched with saturated NH4Cl
  4. additiondiluted with water
  5. extractionThe mixture was extracted with Et2O (3×)
  6. washThe combined Et2O layers were washed with water, brine
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationAfter concentration in vacuo
  9. customthe crude product was purified by flash column chomatography on silica gel
  10. washeluted with 5%-10% EtOAc/Hexane

Sources & evidence

ORD record
ord-a2c4d0cd71d14dcc91d5b245a45199d9
Source dataset
uspto-grants-2005_09
Patent number
US06943180B2

Reaction notes

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