Aluminium lithium hydride → HCID 15169762, compound

HRID 1031265Notes

Reaction equation

HRID 1031265 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1([CH2:13][CH:14]2[N:19]([N:20]=O)[C:18]3[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=3[O:16][CH2:15]2)[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1>C1COCC1>[N:7]1([CH2:13][CH:14]2[N:19]([NH2:20])[C:18]3[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=3[O:16][CH2:15]2)[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 53942973HCID 53942973, compound

Product 1

HCID 15169762HCID 15169762, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 56 g of lithium aluminum hydride in 500 ml of THF was added the (-)-3-(4-morpholinylmethyl)- 4-nitroso-3,4-dihydro-2H-1,4-benzoxazine described above while cooling the reaction mixture to 0° C. with an external cooling bath. When addition was complete the cooling bath was removed, the reaction mixture was stirred for one hour at ambient temperature, cooled again to 0° C. and the excess hydride carefully quenched by the dropwise addition of 5 ml of water, followed by 8 ml of 10% aqueous sodium hydroxide, followed by an additional 5 ml of water. The mixture was stirred, filtered through filter aid, and the filtrate taken to dryness to afford 14.3 g of (-)-3-(4-morpholinylmethyl)-4-amino-3,4-dihydro-2H-1,4-benzoxazine, which was used as such in the next synthetic step without further characterization or purification.

Workup

  1. additionWhen addition
  2. customwas removed
  3. temperaturecooled again to 0° C.
  4. customthe excess hydride carefully quenched by the dropwise addition of 5 ml of water
  5. stirringThe mixture was stirred
  6. filtrationfiltered
  7. filtrationthrough filter aid

Sources & evidence

ORD record
ord-33899350faa049d7a997e26b2a692a34
Source dataset
uspto-grants-1992_04
Patent number
US05109135

Reaction notes

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