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

HRID 1785857Notes

Reaction equation

HRID 1785857 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(#N)C>[O:7]=[C:2]1[NH:1][CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:8])[CH2:3]1

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 6342AcetonitrileSolvent

Procedure

A solution of Example 500A (500 mg, 4.99 mmol) in acetonitrile (25 mL) at room temperature was treated with BOC2O (1198 mg, 5.49 mmol), stirred for 3 hours, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 95:5 ethyl acetate/methanol to provide the desired product.

Workup

  1. concentrationconcentrated
  2. customThe concentrate was purified by flash column chromatography on silica gel with 95:5 ethyl acetate/methanol

Sources & evidence

ORD record
ord-d68fb9f122fd402c93a8c8a38a6587a0
Source dataset
uspto-grants-2009_03
Patent number
US07504512B2

Reaction notes

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