Water → 8-(4-Pyridinyl)-1,4-dioxaspiro[4.5]decan-8-ol

HRID 1193339Notes

Reaction equation

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

Participants

Conditions

Temperature: -78 °C

Procedure

n-BuLi (32 ml, 64.0 mmol, 2 eq, 2 M solution in hexane) was placed in THF (60 ml) and cooled to −78° C. A solution of 4-bromopyridine (6.3 g, 40.0 mmol, 1.25 eq) in THF (50 ml) was slowly added dropwise at that temperature, and stirring was carried out for 1.5 h. A solution of 1,4-dioxaspiro[4.5]decan-8-one (5.0 g, 32.0 mmol, 1 eq) in THF (50 ml) was added likewise at −78° C., and stirring was carried out for 2 h. After monitoring by thin-layer chromatography, the reaction solution was hydrolyzed with water (100 ml), while cooling, and extracted with ethyl acetate (2×200 ml). The combined organic phases were washed with water (100 ml) and sat. NaCl solution (100 ml), dried over sodium sulfate and concentrated under reduced pressure. After purification by column chromatography (silica gel, 2% MeOH in dichloromethane), the desired product was obtained in the form of a light-brown solid. Yield: 64% (6.0 g, 25.53 mmol).

Workup

stirringstirring
waitwas carried out for 2 h
temperaturewhile cooling
extractionextracted with ethyl acetate (2×200 ml)
washThe combined organic phases were washed with water (100 ml) and sat. NaCl solution (100 ml)
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
customAfter purification by column chromatography (silica gel, 2% MeOH in dichloromethane)

Sources & evidence

ORD record: ord-ebf30dcc92c4439c8ffb29c17ab158e1
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680159B2

Reaction notes

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