Aluminium lithium hydride → 8-(Hydroxymethyl)dibenzo[b,f][1,4]oxazepin

HRID 1744935Notes

Reaction equation

HRID 1744935 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1[CH:26]=[CH:25][C:14]2[O:15][C:16]3[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=3[C:18](=O)[NH:19][C:13]=2[CH:12]=1)=O>C1COCC1>[OH:8][CH2:9][C:11]1[CH:26]=[CH:25][C:14]2[O:15][C:16]3[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=3[CH:18]=[N:19][C:13]=2[CH:12]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59737222Methyl 11-oxo-10,11-dihydrodibenzo[b,f][1,4]oxazepine-8-carboxylate

Product 1

HCID 867599558-(Hydroxymethyl)dibenzo[b,f][1,4]oxazepinYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (11 mL, 11 mmole) was slowly added to the solution of 11-Oxo-10,11-dihydro-dibenzo[b,f][1,4]oxazepine-8-carboxylic acid methyl ester (1.346 g, 5 mmole) in THF under N2 at room temperature. The reaction mixture was stirred for 1 hour and 45 minutes then quenched with 2N of HCl until the pH value reaches 2–3. Removed all the THF by rotary evaporation, and extracted the reaction mixture with ethyl acetate for five times, dried the organic layer with sodium sulfate and filtered and concentrated. Obtained the desired compound (white solid) in 46% yield.

Workup

  1. customthen quenched with 2N of HCl until the pH value
  2. customRemoved all the THF
  3. customby rotary evaporation
  4. extractionextracted the reaction mixture with ethyl acetate for five times
  5. dry with materialdried the organic layer with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-aaeb704b2d6b4e9493a13ca513cc7e07
Source dataset
uspto-grants-2006_03
Patent number
US07018997B2

Reaction notes

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