Tetrahydrofuran → 2,2-dimethyl-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazine

Reaction equation

[CH3:1][C:2]1([CH3:13])[O:7][C:6]2[CH:8]=[CH:9][N:10]=[CH:11][C:5]=2[NH:4][C:3]1=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1>>[CH3:1][C:2]1([CH3:13])[O:7][C:6]2[CH:8]=[CH:9][N:10]=[CH:11][C:5]=2[NH:4][CH2:3]1

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 10678883HCID 10678883, compound

HCID 21226445Aluminium lithium hydride

Product 1

HCID 158572102,2-dimethyl-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazineYield 100%

Procedure

By the same method as in the step c) of Example 2, 2,2-dimethyl-4H-pyrido[4,3-b][1,4]oxazin-3-one (120 mg, 0.67 mmol) was reacted with 1.0M Lithium aluminum hydride dissolved in tetrahydrofuran (1.4 ml, 1.4 mmol) to obtain 2,2-dimethyl-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazine (110 mg, quantitative yield).

Sources & evidence

ORD record: ord-856e99661f2f438e95b0e4d7b57d866b
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394792B2

Reaction notes

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