Di-tert-butyl dicarbonate → Tert-butyl 3-oxopiperazine-1-carboxylate

HRID 853637Notes

Reaction equation

HRID 853637 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][C:2]1=[O:7].[O:8](C(OC(C)(C)C)=O)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=O>C(Cl)Cl>[C:12]([O:11][C:9]([N:4]1[CH2:5][CH2:6][NH:1][C:2](=[O:7])[CH2:3]1)=[O:8])([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 231360Piperazin-2-one

Product 1

HCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of piperazine-2-one (1.037 g, 10.4 mmol) in 52 mL of CH2Cl2, was added BOC2O (2.5 g, 11.4 mmol). The reaction became homogeneous after 3 hours when the starting material was completely consumed. The reaction was diluted with CH2Cl2 and the organic layer was washed with water. The solvent was removed in vacuo to yield quantitative amount of product 33 as a white solid. 1H NMR (300 MHz, CDCl3) δ 1.48 (s, 9H), 3.35-3.44 (m, 2H), 3.64 (t, 2H, J=5 Hz), 4.10 (s, 2H), 6.41 (br s, 1H).

Workup

  1. customwhen the starting material was completely consumed
  2. additionThe reaction was diluted with CH2Cl2
  3. washthe organic layer was washed with water
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-02ea5e4f79a14542bd3ce61c68f33558
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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