Aluminium lithium hydride → 4-methyl-6-methoxy-3,4,4a,5,10,10a-hexahydro-2H-naphtho[2,3-b][1,4]oxazine

HRID 975932Notes

Reaction equation

HRID 975932 reaction equation
C(O[C:9]([N:11]1[CH2:16][CH2:15][O:14][CH:13]2[CH2:17][C:18]3[C:23]([CH2:24][CH:12]12)=[C:22]([O:25][CH3:26])[CH:21]=[CH:20][CH:19]=3)=O)C1C=CC=CC=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].CO.CCOC(C)=O>C1COCC1>[CH3:9][N:11]1[CH2:16][CH2:15][O:14][CH:13]2[CH2:17][C:18]3[C:23]([CH2:24][CH:12]12)=[C:22]([O:25][CH3:26])[CH:21]=[CH:20][CH:19]=3

Participants

5

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 21584119Ethylacetate methanolHCID 541517036-methoxy-3,4,4a,5,10,10a-hexahydro-2H-naphtho-[2,3-b][1,4]oxazine-4-carboxylic acid benzyl ester

Product 1

HCID 151310794-methyl-6-methoxy-3,4,4a,5,10,10a-hexahydro-2H-naphtho[2,3-b][1,4]oxazineYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 6-methoxy-3,4,4a,5,10,10a-hexahydro-2H-naphtho-[2,3-b][1,4]oxazine-4-carboxylic acid benzyl ester (0.40 g, 1.1 mmol) in THF was added 2.8 ml of LiAlH4 solution (1.0 M) in THF. The resulting solution was stirred at reflux for 3 h. The reaction mixture was quenched with ice, diluted with EtOAc and filtered through Celite. The organic layer was dried over Na2SO4 and concentrated in vacuo, yielding an oily residue which was subjected to column chromatography (5% MeOH-EtOAc) to yield 0.19 g (75%) of the desired product. 1H NMR (300 MHz, CDCl3): δ 2.07 (m, 1H), 2.28 (m, 1H), 2.37 (s, 3H), 2.49 (m, 1H), 2.77 (m, 2H), 2.97 (dd, 1H, J=5.5, 16.1 Hz), 3.28 (dd, 1H, J=5.5, 17.0 Hz), 3.55 (m, 1H), 3.79 (s, 3H), 3.86 (m, 2H), 6.67 (m, 2H), 7.09 (t, 1H, J=7.8 Hz).

Workup

  1. temperatureat reflux for 3 h
  2. customThe reaction mixture was quenched with ice
  3. additiondiluted with EtOAc
  4. filtrationfiltered through Celite
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customyielding an oily residue which

Sources & evidence

ORD record
ord-25954b6b62c641ec80109d406fafa405
Source dataset
uspto-grants-1997_03
Patent number
US05610174

Reaction notes

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