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

HRID 1945562Notes

Reaction equation

HRID 1945562 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:17](OCC)=[O:18])([CH3:16])[CH3:15])[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[CH2:9][CH2:10][N:11]([C:14]([CH3:16])([CH3:15])[CH2:17][OH:18])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

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 50.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(1-ethoxycarbonyl-1-methylethyl)piperazine-1-carboxylic acid tert-butyl ester (500 mg, 1.67 mmol) in THF (5 mL) at 0° C. was added LiAlH4 (3 mL, 1M in THF) drop wise. The resulting mixture was allowed to stir for 2.5 h then quenched with H2O (0.1 mL), 20% aq. NaOH (0.1 mL) and H2O (0.3 mL). The mixture was diluted with EtOAc and H2O, filtered through Celite® then the organic layer separated, dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, MeOH:DCM, 0-10%) affording the title compound as a colourless oil (217 mg, 50%). 1H NMR (CDCl3, 400 MHz): δ 5.30 (1 H, brd s), 3.42 (6 H, m), 3.35 (4 H, brd s), 2.51 (6 H, brd s), 1.03 (9 H, s)

Workup

  1. customthen quenched with H2O (0.1 mL), 20% aq. NaOH (0.1 mL) and H2O (0.3 mL)
  2. additionThe mixture was diluted with EtOAc and H2O
  3. filtrationfiltered through Celite®
  4. customthe organic layer separated
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by column chromatography (Si—PCC, MeOH:DCM, 0-10%)

Sources & evidence

ORD record
ord-fb95047d44134fd79dc81f53cb004c95
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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