Carbon Dioxide → HCID 89649995, compound

HRID 1479002Notes

Reaction equation

HRID 1479002 reaction equation
C([Li])CCC.[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=2Br)[CH2:15][CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].[C:28](=[O:30])=[O:29]>CCOCC>[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=2[C:28]([OH:30])=[O:29])[CH2:15][CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 89650458HCID 89650458, compoundHCID 178418339Butyllithium

Product 1

HCID 89649995HCID 89649995, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

A 1.6M solution of butyllithium in hexanes (2.5 mL, 4.0 mmol) was added in three portions over 2 hours into a solution of 4-(2-bromo-5-fluoro-benzyl)-piperazine-1-carboxylic acid tert-butyl ester (500 mg, 1.34 mmol) in anhydrous Et2O cooled at −78° C. After one additional hour at −78° C., an excess of dry ice was added and the cooling bath was removed. The reaction mixture was allowed to warm up to RT and was concentrated under vacuum. The residue was taken up with a saturated aqueous solution of NH4Cl and extracted with EtOAc (3×). The organic layers were combined, dried (Na2SO4) and concentrated under vacuum to give the title compound as a yellow oil (391 mg, 78%), used without further purification. HPLC (max plot) 92.1%; Rt 2.47 min. UPLC/MS: (MS+) 339.3 ([M+H]+), (MS−) 337.4 ([M−H]−).

Workup

  1. customthe cooling bath was removed
  2. temperatureto warm up to RT
  3. concentrationwas concentrated under vacuum
  4. extractionextracted with EtOAc (3×)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-813d25759e594a13bdc3b81beebf26ef
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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