Sodium Bicarbonate → 4-(1-Methylcyclopropan-1-yl)piperazine-1-carboxylic acid benzyl ester

HRID 1091307Notes

Reaction equation

HRID 1091307 reaction equation
[CH2:1]([O:8][C:9](=[O:17])[N:10]([CH2:14][CH:15]=O)[CH2:11][CH:12]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18][C:19]1([NH2:22])[CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClC(Cl)C>[CH2:1]([O:8][C:9]([N:10]1[CH2:14][CH2:15][N:22]([C:19]2([CH3:18])[CH2:21][CH2:20]2)[CH2:12][CH2:11]1)=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 116511491-MethylcyclopropanamineHCID 15009275HCID 15009275, compound

Product 1

HCID 665917424-(1-Methylcyclopropan-1-yl)piperazine-1-carboxylic acid benzyl esterYield 49%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Bis-(2-oxoethyl)carbamicacidbenzylester (0.90 g, 3.81 mmol) and 1-methyl-cyclopropylamine (0.41 g, 3.81 mmol) were dissolved in dichloroethane (20 mL), and sodium triacetoxyborohydride (3.23 g, 15.24 mmol) was added thereto. The mixture was stirred for 4 days at room temperature. A saturated aqueous solution of sodium hydrogen carbonate (20 mL) was added to the reaction liquor, and the mixture was stirred for 20 minutes, and then extracted with methylene chloride. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and then the solvent was concentrated under reduced pressure. The obtained residue was purified by flash chromatography (Flash Chromatography System from Biotage AB, column size: 25S, n-hexane/ethyl acetate=5/1 to ethyl acetate), to obtain the title compound (509 mg, 49%) as an oily matter.

Workup

  1. stirringthe mixture was stirred for 20 minutes
  2. extractionextracted with methylene chloride
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationthe solvent was concentrated under reduced pressure
  6. customThe obtained residue was purified by flash chromatography (Flash Chromatography System from Biotage AB, column size: 25S, n-hexane/ethyl acetate=5/1 to ethyl acetate)

Sources & evidence

ORD record
ord-bbb4f28b493b41549df7873c21e4a41c
Source dataset
uspto-grants-2012_03
Patent number
US08129366B2

Reaction notes

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