Pyrrolidine → HCID 57493998, compound

HRID 1689883Notes

Reaction equation

HRID 1689883 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[Li]CCCC.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][N:21]([C:24]([C:27](OCC)=[O:28])([CH3:26])[CH3:25])[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]>C1COCC1>[C:11]([O:15][C:16]([N:18]1[CH2:19][CH2:20][N:21]([C:24]([CH3:26])([CH3:25])[C:27](=[O:28])[N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:22][CH2:23]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 57420344HCID 57420344, compoundHCID 178418339Butyllithium

Product 1

HCID 57493998HCID 57493998, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Amine preparation: to pyrrolidine (390 uL) in dry THF (4 mL) at 0° C. was added nBuLi (1.86 ml) The reaction mixture was stirred for 5 minutes and then 4-(1-ethoxycarbonyl-1-methyl-ethyl)-piperazine-1-carboxylic acid tert-butyl ester (700 mg) in THF (5 mL) was added. The reaction mixture was stirred at room temperature for 24 h and then quenched with aqueous ammonium chloride, extracted into DCM, washed with water, dried (MgSO4) and the solvent removed in vacuo to yield 4-(1,1-dimethyl-2-oxo-2-pyrrolidin-1-yl-ethyl)-piperazine-1-carboxylic acid tert-butyl ester (745 mg). Removal of the BOC group with HCl yielded the desired compound, which was isolated as the hydrochloride salt.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 24 h
  2. customquenched with aqueous ammonium chloride
  3. extractionextracted into DCM
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-d1bb99bbe35e43519ba88a9d663b734f
Source dataset
uspto-grants-2012_04
Patent number
US08153629B2

Reaction notes

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