6-methoxy-4a,5,10,10a-tetrahydro-4H-naphto[2,3-b][1,41oxazin-3-one → 6-methoxy-3,4,4a,5,10,10 a-hexahydro-2H-naphtho-[2,3-b][1,4]oxazine

HRID 975930Notes

Reaction equation

HRID 975930 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:4]=1[CH2:5][CH:6]1[NH:11][C:10](=O)[CH2:9][O:8][CH:7]1[CH2:13]2.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][O:2][C:3]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:4]=1[CH2:5][CH:6]1[NH:11][CH2:10][CH2:9][O:8][CH:7]1[CH2:13]2

Participants

4

Reactant 2

HCID 151310756-methoxy-4a,5,10,10a-tetrahydro-4H-naphto[2,3-b][1,41oxazin-3-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 151310776-methoxy-3,4,4a,5,10,10 a-hexahydro-2H-naphtho-[2,3-b][1,4]oxazineYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 6-methoxy-4a,5,10,10a-tetrahydro-4H-naphto[2,3-b][1,41oxazin-3-one (1.4 g, 6.0 mmol) in 100 ml of THF was added 10 ml of LiAlH4 solution in THF (10 mmol). The resulting solution was stirred for 2 h at reflux. The reaction was quenched with ice and the reaction mixture was then diluted with EtOAc. Filtration of the reaction mixture provided a clean organic layer which was concentrated in vacuo to yield 1.2 g (92%) of the desired product as a colorless oil. 1H NMR (300 MHz, CDCl3): δ 1.85 (s, 1H), 2.34 (dd, 1H, J=12.0, 17.0 Hz), 2.78-3.16 (m, 6H), 3.50 (ddd, 1H, J=5.2, 6.8, 10.5 Hz), 3.74 (m, 1H), 3.81 (s, 3H), 3.94 (m, 1H), 6.70 (m, 2H), 7.16 (t, 1H, J=7.6 Hz).

Workup

  1. temperatureat reflux
  2. customThe reaction was quenched with ice
  3. additionthe reaction mixture was then diluted with EtOAc
  4. filtrationFiltration of the reaction mixture
  5. customprovided a clean organic layer which
  6. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-a924fd53fd6e4f4dabf3cc6537dec22b
Source dataset
uspto-grants-1997_03
Patent number
US05610174

Reaction notes

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