Aluminium lithium hydride → HCID 59153168, compound

HRID 2355279Notes

Reaction equation

HRID 2355279 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:12][C:11]=1[Cl:25]>O1CCCC1>[C:21]([O:20][C:18](=[O:19])[NH:17][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][OH:8])=[C:11]([Cl:25])[CH:12]=1)([CH3:24])([CH3:22])[CH3:23]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59383085HCID 59383085, compound

Product 1

HCID 59153168HCID 59153168, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

Add 1M lithium aluminum hydride in tetrahydrofuran (32 mL, 32 mmol) to anhydrous tetrahydrofuran (240 mL) at room temperature under argon gas, cool to 0° C. and add slowly a solution of 4-(tert-butoxycarbonylamino-methyl)-2-chloro-benzoic acid methyl ester (3.2 g, 10.7 mmol) in tetrahydrofuran (120 mL). The reaction mixture is stirred at 0° C. for 45 min. Quench the reaction mixture with saturated aqueous ammonium chloride and extract with ethyl acetate (3×). Combine the organic layers, wash with brine, dry over sodium sulfate, and concentrate. Purify the residue by chromatography (silica gel) eluting with 35% ethyl acetate/hexane to give the title compound (2.1 g, 7.7 mmol). MS (m/z): 294 (M+23).

Workup

  1. customQuench the reaction mixture with saturated aqueous ammonium chloride
  2. extractionextract with ethyl acetate (3×)
  3. washCombine the organic layers, wash with brine
  4. dry with materialdry over sodium sulfate
  5. concentrationconcentrate
  6. customPurify the residue by chromatography (silica gel)
  7. washeluting with 35% ethyl acetate/hexane

Sources & evidence

ORD record
ord-3281b2fc2099444e9253c65f18875c31
Source dataset
uspto-grants-2010_07
Patent number
US07754742B2

Reaction notes

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