Water → 3-[4-({[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}methyl)-6-(methyloxy)-2-pyridinyl]-1-propanol

HRID 15350Notes

Reaction equation

[CH3:1][C:2]([Si:5]([CH3:26])([CH3:25])[O:6][CH2:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[N:11]=[C:10]([CH2:16][CH2:17][C:18](OCCCC)=[O:19])[CH:9]=1)([CH3:4])[CH3:3].[H-].[H-].[H-].[H-].[Li+].[Al+3].O>C1COCC1>[CH3:4][C:2]([Si:5]([CH3:26])([CH3:25])[O:6][CH2:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[N:11]=[C:10]([CH2:16][CH2:17][CH2:18][OH:19])[CH:9]=1)([CH3:1])[CH3:3]

Participants

Conditions

Temperature: -20 °C

Procedure

A solution of butyl 3-[4-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-6-(methyloxy)-2-pyridinyl]propanoate (4.76 g, 12.49 mmol) in THF (120 ml) was treated with LiAlH4 soln (1M in THF, 12.49 ml, 12.49 mmol) at −78° C. The reaction mixture was allowed warm to −20° C. and after stirring at −20° C. for 15 min, the mixture was treated with water (9 ml) and allowed to stir for 1 h before being filtered and evaporated to give a slightly impure product (3.98 g, 102%).

Workup

stirringto stir for 1 h
filtrationbefore being filtered
customevaporated

Sources & evidence

ORD record: ord-11c36c563435473db174b2975e99cded
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732461B2

Reaction notes

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