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

HRID 2365179Notes

Reaction equation

HRID 2365179 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-a6d1060ddb044a708d6c1687db3776b0
Source dataset
uspto-grants-2014_04
Patent number
US08697693B2

Reaction notes

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