Aluminium lithium hydride → tert-Butyl 4-aminopiperazine-1-carboxylate

HRID 2400950Notes

Reaction equation

HRID 2400950 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([N:14]=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([NH2:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58919487HCID 58919487, compound

Product 1

HCID 22029174tert-Butyl 4-aminopiperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 4-nitrosopiperazine-1-carboxylic acid tert-butyl ester (7.4 mmol) in THF (100 mL) was added LAH (2.5 eq.) portionwise at 0° C. The solution was warmed to rt and stirred overnight, then quenched by the dropwise addition of a saturated solution of potassium sodium tartrate. The aqueous solution was extracted several times with DCM. The organic layer was dried (Na2SO4) and concentrated at 25° C. to afford 4-aminopiperazine-1-carboxylic acid tert-butyl ester as a white solid.

Workup

  1. customquenched by the dropwise addition of a saturated solution of potassium sodium tartrate
  2. extractionThe aqueous solution was extracted several times with DCM
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated at 25° C.

Sources & evidence

ORD record
ord-d1eb580ed411444481cc57fdb35f0890
Source dataset
uspto-grants-2014_08
Patent number
US08796256B2

Reaction notes

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