Acetic Acid → (R)-1-Boc-2-methyl-4-isopropylpiperazine

HRID 879600Notes

Reaction equation

HRID 879600 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@H:9]1[CH3:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:29][C:30]([CH3:32])=O.C(O)(=O)C>CN(C=O)C.O>[C:1]([N:8]1[CH2:13][CH2:12][N:11]([CH:30]([CH3:32])[CH3:29])[CH2:10][C@H:9]1[CH3:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 10262201tert-Butyl (2R)-2-methylpiperazine-1-carboxylate

Product 1

HCID 86700416(R)-1-Boc-2-methyl-4-isopropylpiperazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To (R)-1-Boc-2-methylpiperazine (200.0 mg, 0.999 mmol) and sodium triacetoxyborohydride (444.5 mg, 2.097 mmol) in DMF (5 mL) was added acetone (116 mg, 0.147 mL, 1.997 mmol) and acetic acid (90.0 mg, 86 μL, 1.498 mmol). The reaction mixture was heated at 60° C. for 1 h. The reaction mixture was diluted with water and extracted three times with diethyl ether. The combined organics were dried over sodium sulfate, filtered, concentrated, and used without further purification. LCMS-ESI+: calc'd for C13H27N2O2 (M+H+): 243.2; Found: 243.1 (M+H+).

Workup

  1. extractionextracted three times with diethyl ether
  2. dry with materialThe combined organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customused without further purification

Sources & evidence

ORD record
ord-b511094160684e6f856a61165f51b79d
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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