Aluminium lithium hydride → HCID 58442814, compound

HRID 41621Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:19]([C:20](OC)=[O:21])=[CH:18][N:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:15]=[CH:16][N:17]=[CH:18][C:19]=2[CH2:20][OH:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of methyl 4-(1-(tert-butoxycarbonyl)piperidin-4-yl)nicotinate (2.6 g, 8.1 mmol, 1.0 eq.) in THF (50 mL) was added dropwise to a solution of lithium aluminium hydride (617 mg, 16.3 mmol, 2.0 eq.) in THF (100 mL) at 0° C. under nitrogen. The resulting solution was stirred for 0.5 hours while the temperature was maintained at 0° C. in an ice/salt bath. The reaction was then quenched with water (0.6 mL) and 15% NaOH (1.8 mL). The mixture was stirred for 10 minutes. The solids were filtered and washed with EtOAc (30 mL). The filtrate was dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with EtOAc/MeOH (10:1) to yield the title compound (1.6 g) as a white solid. ES m/z: [M+H]+293.

Workup

customThe reaction was then quenched with water (0.6 mL) and 15% NaOH (1.8 mL)
stirringThe mixture was stirred for 10 minutes
filtrationThe solids were filtered
washwashed with EtOAc (30 mL)
dry with materialThe filtrate was dried over anhydrous Na2SO4
concentrationconcentrated under vacuum
washeluted with EtOAc/MeOH (10:1)

Sources & evidence

ORD record: ord-a5933b5ebfaf469f83ba3349ee302da9
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530663B2

Reaction notes

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