Cyclobutanone → HCID 59454538, compound

HRID 880396Notes

Reaction equation

HRID 880396 reaction equation
[CH3:1][C:2]1([CH3:15])[NH:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[C:16]1(=O)[CH2:19][CH2:18][CH2:17]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(O)(=O)C>[CH:16]1([N:7]2[CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3][C:2]2([CH3:15])[CH3:1])[CH2:19][CH2:18][CH2:17]1

Participants

6

Reactant 3

HCID 14496CyclobutanoneHCID 5049666Sodium triacetoxyborohydrideHCID 227103871-Boc-3,3-dimethylpiperazine

Product 1

HCID 59454538HCID 59454538, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
40 °C

Procedure

Tert-butyl 3,3-dimethylpiperazine-1-carboxylate (413 mg, 1.65 mmol) was dissolved in DCE (15 mL). TEA (1.148 mL, 8.23 mmol) was added, followed by cyclobutanone (231 mg, 3.29 mmol) and sodium triacetoxyborohydride (524 mg, 2.47 mmol). The reaction mixture was stirred for 5 h and a few drops of acetic acid were added. The reaction mixture was heated at 40° C. for 4 days, cooled to rt, washed with sat NaHCO3, dried over MgSO4, filtered and concentrated under reduced pressure to give a dark yellow oil. The crude title compound was used in the next step without further purification.

Workup

  1. temperaturecooled to rt
  2. washwashed
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give a dark yellow oil
  7. customThe crude title compound was used in the next step without further purification

Sources & evidence

ORD record
ord-0b8d3ebda5a74d39b2ada77e11564112
Source dataset
uspto-grants-2015_03
Patent number
US08993577B2

Reaction notes

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