Aluminium lithium hydride → HCID 58442818, compound

HRID 41625Notes

Reaction equation

C[O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:20]([O:19][C:17]([N:14]1[CH2:15][CH2:16][CH:11]([C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[CH2:3][OH:2])[CH2:12][CH2:13]1)=[O:18])([CH3:23])([CH3:21])[CH3:22]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 3′,4′,5′,6′-tetrahydro-2′H-[3,4′]bipyridinyl-4,1′-dicarboxylic acid 1′-t-butyl ester 4-methyl ester (3.3 g, 8.2 mmol, 1.0 eq.) in THF (50 mL) was added dropwise to a solution of LiAlH4 (590 mg, 15.5 mmol, 1.5 eq.) in THF (50 mL) at 0° C. under nitrogen. The resulting solution was stirred for 10 minutes at 0° C. The reaction was then quenched with water (0.6 mL) and 15% NaOH (1.8 mL). The solids were filtered. The mixture was dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with EtOAc/PE (1:1) to yield the title compound (1.8 g) as a white solid. MS m/z: [M+H]+ calcd for C16H25N2O3, 293. found 293.

Workup

customThe reaction was then quenched with water (0.6 mL) and 15% NaOH (1.8 mL)
filtrationThe solids were filtered
dry with materialThe mixture was dried over anhydrous Na2SO4
concentrationconcentrated under vacuum
washeluted with EtOAc/PE (1:1)

Sources & evidence

ORD record: ord-6c0ddbddec85402aa6b0bbb46c0beffe
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530663B2

Reaction notes

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