Aluminium lithium hydride → HCID 86714536, compound

HRID 1843422Notes

Reaction equation

HRID 1843422 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([O:11][C:12]([N:14]([CH2:23][CH3:24])[C:15]([CH3:22])([CH3:21])[C:16](OCC)=[O:17])=[O:13])([CH3:10])([CH3:9])[CH3:8]>C1COCC1>[CH2:23]([N:14]([C:15]([CH3:21])([CH3:22])[CH2:16][OH:17])[C:12](=[O:13])[O:11][C:7]([CH3:10])([CH3:8])[CH3:9])[CH3:24]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86714537HCID 86714537, compound

Product 1

HCID 86714536HCID 86714536, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of LiAlH4 (760 mg, 20 mmol, 1.0 equiv) in THF (50 mL) was added ethyl 2-(tert-butoxycarbonyl(ethyl)amino)-2-methylpropanoate (5.18 g, 20 mmol, 1 equiv) at 0° C. under N2. The mixture was stirred for 4 h at 0° C. It was quenched with ice/water at 0° C., then extracted with ethyl acetate (50 mL×3). The organic layers were combined, washed with brine, dried over Na2SO4 and concentrated. The residue was purified by a silica gel column (pet. ether/ethyl acetate=4/1) to give 2 g (45%) of tert-butyl ethyl(1-hydroxy-2-methylpropan-2-yl)carbamate as a colorless oil.

Workup

  1. customIt was quenched with ice/water at 0° C.
  2. extractionextracted with ethyl acetate (50 mL×3)
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by a silica gel column (pet. ether/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-99a9cb67a20e40edb29bd6fa9a5cbb03
Source dataset
uspto-grants-2015_02
Patent number
US08946241B2

Reaction notes

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