Lithium Hexamethyldisilazide → HCID 58017563, compound

HRID 1642766Notes

Reaction equation

HRID 1642766 reaction equation
Br[CH2:2][CH2:3][C@H:4]([NH:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[N:11]1([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:2][CH2:3][C@@H:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[NH:10]1

Participants

4

Reactant 2

HCID 2733832Lithium HexamethyldisilazideHCID 58017529HCID 58017529, compound

Product 1

HCID 58017563HCID 58017563, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of slightly impure tert-butyl 2-[(1S)-3-bromo-1-(ethoxycarbonyl)propyl]hydrazinecarboxylate (1.57 g, 4.83 mmol) in dry THF (50 mL) at 0° C. was added LiHMDS (1 M in THF, 4.83 mmol, 4.83 mL). The solution was allowed to attain rt and was then stirred for 2 h. The reaction was quenched by addition of saturated NH4Cl(aq) and diluted with TBME. The phases were separated, the organic phase was dried, filtered and evaporated. The residue was purified using flash chromatography (DCM/EtOAc 4:1, 1:1) to give the pure 1-tert-butyl 3-ethyl (3S)-pyrazolidine-1,3-dicarboxylate (610 mg, 52%) as an oil.

Workup

  1. customto attain rt
  2. customThe reaction was quenched by addition of saturated NH4Cl(aq)
  3. additiondiluted with TBME
  4. customThe phases were separated
  5. customthe organic phase was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified

Sources & evidence

ORD record
ord-870187e42127489f8f3f39a2bebc6a42
Source dataset
uspto-grants-2012_02
Patent number
US08119673B2

Reaction notes

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