Aluminium lithium hydride → 1,1-Dimethylethyl 4-(2-hydroxy-1,1-dimethylethyl)-1-piperazinecarboxylate

HRID 888926Notes

Reaction equation

HRID 888926 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][N:17]([C:20]([C:23](OCC)=[O:24])([CH3:22])[CH3:21])[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>O1CCCC1>[C:7]([O:11][C:12]([N:14]1[CH2:15][CH2:16][N:17]([C:20]([CH3:22])([CH3:21])[CH2:23][OH:24])[CH2:18][CH2:19]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57420344HCID 57420344, compound

Product 1

HCID 574203451,1-Dimethylethyl 4-(2-hydroxy-1,1-dimethylethyl)-1-piperazinecarboxylateYield 39.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of lithium aluminium hydride powder (0.324 g) in anhydrous tetrahydrofuran (30 mL) at 0° C. under argon was added 4-(1-ethoxycarbonyl-1-methyl-ethyl)-piperazin-1-carboxylic acid tert-butyl ester (1.28 g). The reaction mixture was allowed to warm to room temperature and stirred for 2 hours, then quenched with saturated aqueous ammonium chloride (10 mL). The reaction mixture was partitioned between water and dichloromethane and the combined organic layers washed with brine and dried (MgSO4). The solution was evaporated to give 4-(2-hydroxy-1,1-dimethyl-ethyl)-piperazin-1-carboxylic acid tert-butyl ester (0.43 g).

Workup

  1. customquenched with saturated aqueous ammonium chloride (10 mL)
  2. customThe reaction mixture was partitioned between water and dichloromethane
  3. washthe combined organic layers washed with brine
  4. dry with materialdried (MgSO4)
  5. customThe solution was evaporated

Sources & evidence

ORD record
ord-9e52ce89e97f4fe79edf685e842a807e
Source dataset
uspto-grants-2012_08
Patent number
US08252792B2

Reaction notes

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