Aluminium lithium hydride → (R)-3-(benzyl((S)-1-phenylethyl)amino)-3-(6-methylpyridin-3-yl)propan-1-ol

HRID 241856Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([N:14]([C@H:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH3:32])[C@@H:15]([C:24]1[CH:25]=[N:26][C:27]([CH3:30])=[CH:28][CH:29]=1)[CH2:16][C:17](OC(C)(C)C)=[O:18])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[CH2:7]([N:14]([C@H:31]([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[CH3:32])[C@@H:15]([C:24]1[CH:25]=[N:26][C:27]([CH3:30])=[CH:28][CH:29]=1)[CH2:16][CH2:17][OH:18])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of LiAlH4 (1.24 g, 32.79 mmol) in THF (80 mL) at 0° C., was added dropwise a solution of (R)-tert-butyl 3-(benzyl((S)-1-phenylethyl)amino)-3-(6-methylpyridin-3-yl)propanoate (4.7 g, 10.93 mmol) in THF and was heated to 75° C. After 4 h, the reaction mixture was quenched with EtOAc and filtered. The filtrate was washed with excess EtOAc and dried under high vacuum to afford a residue. Purification of the residue by column chromatography (neutral Al2O3, Et2O/Pet ether 15:85) afforded the title compound. MS: 361.5 ([M−H]+);

Workup

customthe reaction mixture was quenched with EtOAc
filtrationfiltered
washThe filtrate was washed with excess EtOAc
customdried under high vacuum
customto afford a residue
customPurification of the residue by column chromatography (neutral Al2O3, Et2O/Pet ether 15:85)

Sources & evidence

ORD record: ord-95ef64823a9f49e393d43415f72467d0
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653091B2

Reaction notes

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