Lithium aluminum hydride → HCID 117777515, compound

HRID 928547Notes

Reaction equation

HRID 928547 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[CH:9][C:10]([C:23](OC)=[O:24])=[C:11]3[C:16]=2[O:15][CH2:14][CH:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[NH:12]3)=[C:5]([CH3:27])[O:4][N:3]=1.[AlH4-].[Li+]>O1CCCC1>[CH3:1][C:2]1[C:6]([C:7]2[C:16]3[O:15][CH2:14][CH:13]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[NH:12][C:11]=3[C:10]([CH2:23][OH:24])=[CH:9][CH:8]=2)=[C:5]([CH3:27])[O:4][N:3]=1

Participants

4

Reactant 2

HCID 28112Lithium aluminum hydrideHCID 117777432HCID 117777432, compound

Product 1

HCID 117777515HCID 117777515, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of methyl 8-(3,5-dimethylisoxazol-4-yl)-3-phenyl-3,4-dihydro-2H-1,4-benzoxazine-5-carboxylate (0.150 g, 0.412 mmol) in tetrahydrofuran (4.50 mL) at 0° C. was treated with 1.0 M lithium tetrahydroaluminate in THF (0.823 mL, 0.823 mmol) dropwise. After complete addition the mixture was stirred at 0° C. for 15 min. The reaction mixture was quenched with saturated ammonium chloride solution (20 mL), warmed to R.T., and extracted with ethyl acetate (2×20 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated to give a colorless residue. Purification by flash column chromatography (100% hexanes to 70% EtOAc [containing 5% methanol]/30% hexanes) gave the desired product (0.13 g, 94%) as a white foam. LCMS calculated for C20H21N2O3 (M+H)+: m/z=337.2. found: 337.2.

Workup

  1. additionAfter complete addition the mixture
  2. customThe reaction mixture was quenched with saturated ammonium chloride solution (20 mL)
  3. temperaturewarmed to R.T.
  4. extractionextracted with ethyl acetate (2×20 mL)
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a colorless residue
  9. customPurification by flash column chromatography (100% hexanes to 70% EtOAc [containing 5% methanol]/30% hexanes)

Sources & evidence

ORD record
ord-1efebd103781407a9ad5609de4c8163f
Source dataset
uspto-grants-2016_03
Patent number
US09290514B2

Reaction notes

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