Aluminium lithium hydride → 9-[(Phenylmethyl)oxy]-2,3,4,5-tetrahydro-1,4-benzoxazepine

HRID 1514221Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([CH2:13][O:14][C:15]2[C:25]3[O:24][CH2:23][CH2:22][NH:21][C:20](=O)[C:19]=3[CH:18]=[CH:17][CH:16]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C1COCC1>[C:7]1([CH2:13][O:14][C:15]2[C:25]3[O:24][CH2:23][CH2:22][NH:21][CH2:20][C:19]=3[CH:18]=[CH:17][CH:16]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 60 °C

Procedure

1M Lithium aluminum hydride (60 ml, 60.0 mmol) in THF was added to a stirred solution of 9-[(phenylmethyl)oxy]-3,4-dihydro-1,4-benzoxazepin-5(2H)-one (Preparation 59) (7.4 g, 27.5 mmol) in THF (150 ml) under argon and heated at 60° C. for 2 hours then cooled and quenched by careful addition of 100 ml of 2M sodium hydroxide with ice bath cooling and the resulting suspension filtered, the solids washed with water and EtOAc and the organic dried (magnesium sulphate) and evaporated to give 7.01 g of white solid. MS (ES): C16H17NO2 requires 255; found 256 [M+H]+.

Workup

temperaturethen cooled
customquenched by careful addition of 100 ml of 2M sodium hydroxide with ice bath
temperaturecooling
filtrationthe resulting suspension filtered
washthe solids washed with water and EtOAc
dry with materialthe organic dried (magnesium sulphate)
customevaporated

Sources & evidence

ORD record: ord-919d56a2d5de4a5ab59eb33f32434aed
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222245B2

Reaction notes

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