Aluminium lithium hydride → HCID 59403541, compound

HRID 1514195Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([CH2:13][O:14][C:15]2[CH:26]=[CH:25][C:18]3[C:19](=O)[NH:20][CH2:21][CH2:22][O:23][C:17]=3[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[CH:26]=[CH:25][C:18]3[CH2:19][NH:20][CH2:21][CH2:22][O:23][C:17]=3[CH:16]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 60 °C

Procedure

1M Lithium aluminium hydride (62.4 ml, 62.4 mmol) in THF was added under argon to a stirred solution of 8-[(phenylmethyl)oxy]-3,4-dihydro-1,4-benzoxazepin-5(2H)-one (Preparation 27) (8.39 g, 31.2 mmol) in THF (150 ml) with ice bath cooling over 5 minutes. The resulting solution was heated with stirring at 60° C. for 3 hours. The reaction was cooled and carefully quenched by slow addition with ice cooling of 150 ml of 2M sodium hydroxide followed by 150 ml of EtOAc. The organics were separated and aqueous extracted with 100 ml of EtOAc. The combined organic extracts were dried (magnesium sulphate) and evaporated to give the title compound (7.53 g) as a light coloured oil. MS (ES) C16H17NO2 requires 255; found 256 [M+H]+.

Workup

temperaturecooling over 5 minutes
temperatureThe resulting solution was heated
temperatureThe reaction was cooled
customcarefully quenched by slow addition with ice
temperaturecooling of 150 ml of 2M sodium hydroxide
customThe organics were separated
extractionaqueous extracted with 100 ml of EtOAc
dry with materialThe combined organic extracts were dried (magnesium sulphate)
customevaporated

Sources & evidence

ORD record: ord-d7072acb7be646208263080ab6a7f676
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222245B2

Reaction notes

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