Aluminium lithium hydride → HCID 67398160, compound

HRID 450429Notes

Reaction equation

C([O:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:17][CH:16]=2)=[CH:10][N:9]=1)=O)(C)(C)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:25]([O:24][C:22](=[O:23])[NH:21][C:18]1[CH:17]=[CH:16][C:15]([O:14][C:11]2[CH:10]=[N:9][C:8]([CH2:6][OH:5])=[CH:13][CH:12]=2)=[CH:20][CH:19]=1)([CH3:28])([CH3:26])[CH3:27]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 5-(4-t-butoxycarbonylamino-phenoxy)-pyridine-2-carboxylic acid t-butyl ester (0.5 g, 1.3 mmol) in THF (2.0 ml) was added dropwise to a 0° C. suspension of LiAlH4 (0.1 g, 2.6 mmol) in dry THF (5.0 ml). The reaction was stirred at 0° C. for 2 h and was quenched with 10% aqueous NaOH (1.0 mL). The mixture was filtered and the filtrate was concentrated in vacuo to give [4-(6-hydroxymethyl-pyridin-3-yloxy)-phenyl]-carbamic acid t-butyl ester (0.38 g, 92% yield). MS (ESI) m/z: (M+H+) 317.2.

Workup

customwas quenched with 10% aqueous NaOH (1.0 mL)
filtrationThe mixture was filtered
concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-8670c49218f543fbbc27ba872d8b3721
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486951B2

Reaction notes

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