Aluminium lithium hydride → HCID 22730187, compound

HRID 2356084Notes

Reaction equation

HRID 2356084 reaction equation
[C:1]([C:3]1([S:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)#[N:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:2][CH2:1][C:3]1([S:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22730851HCID 22730851, compound

Product 1

HCID 22730187HCID 22730187, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of Example 252A (1.0 g, 3.1 mmol) in THF (5 mL) at 0° C. was treated dropwise with 1M LiAlH4 in THF (3 mL), warmed to room temperature, stirred for 2 hours, quenched with methanol (1 mL), treated with 1N NaOH (50 mL), and extracted with ethyl acetate (3×100 mL). The combined extracts were washed with water and brine, dried (Na2SO4), filtered, and concentrated to provide the desired product. MS (APCI) m/e 323 (M+H)+.

Workup

  1. customquenched with methanol (1 mL)
  2. additiontreated with 1N NaOH (50 mL)
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. washThe combined extracts were washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e7457270899c47888c67f5c6084eb1cc
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

Loading…