Aluminium lithium hydride → [2-(5-Hydroxy-2-oxo-imidazolidin-1-yl)-ethyl]-carbamic acid tert-butyl ester

HRID 507506Notes

Reaction equation

HRID 507506 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][CH2:9][N:10]1[C:14](=[O:15])[CH2:13][NH:12][C:11]1=[O:16])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][CH2:9][N:10]1[CH:14]([OH:15])[CH2:13][NH:12][C:11]1=[O:16])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57428812[2-(2,5-Dioxo-imidazolidin-1-yl)-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 60204244[2-(5-Hydroxy-2-oxo-imidazolidin-1-yl)-ethyl]-carbamic acid tert-butyl esterYield 82.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

[2-(2,5-Dioxo-imidazolidin-1-yl)-ethyl]-carbamic acid tert-butyl ester (14.6 g, 60 mmol) was dissolved in THF (1.5 L) and treated with 1.0 M LiAlH4 in THF (77 mL, 77 mmol) added dropwise. The initial vigorous effervescence subsided and the solution became opaque white. The mixture was stirred for 16 h and then quenched (i. 2.0 mL of water; ii. 2.0 mL of 4 M aqueous NaOH; iii. 10 mL of water). The mixture was filtered and the resulting filtrate concentrated to give 12.1 g of solid. This was dissolved in 100 mL of hot EtOAc and applied (hot) to 250 g of silica pre-washed with EtOAc. The product was isolated by elution with EtOAc→2% MeOH/EtOAc→5% MeOH/EtOAc as a white solid (7.85 g, 53%). The compound has poor solubility in a number of organic solvents.

Workup

  1. additionadded dropwise
  2. customquenched (i. 2.0 mL of water; ii. 2.0 mL of 4 M aqueous NaOH; iii. 10 mL of water)
  3. filtrationThe mixture was filtered
  4. concentrationthe resulting filtrate concentrated

Sources & evidence

ORD record
ord-01046a11f6eb42f98a7db136f1f11d4f
Source dataset
uspto-grants-2010_08
Patent number
US07786132B2

Reaction notes

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