Cyclobutanone → Tert-butyl 4-cyclobutylpiperazine-1-carboxylate

HRID 734319Notes

Reaction equation

HRID 734319 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:14]1(=O)[CH2:17][CH2:16][CH2:15]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]2[CH2:17][CH2:16][CH2:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 14496CyclobutanoneHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 57423951Tert-butyl 4-cyclobutylpiperazine-1-carboxylateYield 84.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-tert-Butoxycarbonyl-piperazine (5.6 g) was dissolved in dry DCM (100 ml) followed by the addition of cyclobutanone (2.10 g). The reaction mixture was stirred at rt for 30 min. Sodium triacetoxyborohydride (6.37 g) was added portion-wise over 15 min. The mixture was then stirred at rt overnight to give a black solution. The reaction mixture was washed with 1N NaOH (70 ml) and the DCM layer was separated, dried (MgSO4) and filtered. The filtrate was evaporated to dryness to give the subtitled compound as an oil (6.1 g) 1H NMR δ [DMSO-d6]: 1.39 (6H, s), 1.68-1.87 (4H, m), 1.9-2.01 (2H, m), 2.15-2.2 (3H, m), 2.5 (1H, m), 2.6-2.78 (1H, m), 3.18-3.3 (4H, m).

Workup

  1. stirringThe mixture was then stirred at rt overnight
  2. customto give a black solution
  3. washThe reaction mixture was washed with 1N NaOH (70 ml)
  4. customthe DCM layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-92731af030184bb99b673c413f2a6c0a
Source dataset
uspto-grants-2009_09
Patent number
US07592347B2

Reaction notes

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