Diethyl Ether → HCID 13055755, compound

HRID 647465Notes

Reaction equation

HRID 647465 reaction equation
[CH2:1]([C@@:3]1([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20]C)[CH:15]=2)[CH2:8][N:7]([CH3:9])[C@H:6]2[CH2:10][CH2:11][CH2:12][CH2:13][C@@H:5]2[O:4]1)[CH3:2].[H-].C([Al+]CC(C)C)C(C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+].CCOCC>C1(C)C=CC=CC=1>[CH2:1]([C@@:3]1([C:14]2[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=2)[CH2:8][N:7]([CH3:9])[C@H:6]2[CH2:10][CH2:11][CH2:12][CH2:13][C@@H:5]2[O:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 9357Potassium Sodium TartrateHCID 13055752HCID 13055752, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 13055755HCID 13055755, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(2R*,4aS*,8aS*)-2-Ethyl-2-(3-methoxyphenyl)-4-methyloctahydro-2H-1,4-benzoxazine (0.5 g) in dry toluene (5 cm3) was added under nitrogen to di-isobutylaluminium hydride (20% in toluene, 1.2 M, 15 cm3) at room temperature. The mixture was then heated to reflux under nitrogen for 51/2 hr. The mixture was cooled in ice to 0° and treated cautiously with saturated Rochelle salt solution (75 cm3) and the mixture was stirred for 1 hr. Ether (30 cm3) was added and the phases were separated. The aqueous phase was then treated with an equal volume of saturated ammonium chloride solution and was extracted with further ether. The combined organic phases were dried (Na2SO4) and evaporated, leaving impure title compound base as a cloudy oil which crystallised to a pale yellow mass (0.45 g).

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux under nitrogen for 51/2 hr
  3. temperatureThe mixture was cooled in ice to 0°
  4. customthe phases were separated
  5. additionThe aqueous phase was then treated with an equal volume of saturated ammonium chloride solution
  6. extractionwas extracted with further ether
  7. dry with materialThe combined organic phases were dried (Na2SO4)
  8. customevaporated

Sources & evidence

ORD record
ord-cce4c12362924410a7f24bb3f65cee79
Source dataset
uspto-grants-1983_10
Patent number
US04409218

Reaction notes

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