Ethylene Oxide → 3-(4-Chloro-6-morpholin-4-yl-pyrid-2-yl)-propan-1-ol

HRID 252984Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[N:3]=1.C([Li])CCC.[O:20]1[CH2:22][CH2:21]1>O1CCCC1>[Cl:8][C:6]1[CH:5]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[N:3]=[C:2]([CH2:1][CH2:22][CH2:21][OH:20])[CH:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

2-Methyl-4-chloro-6-morpholino-pyridine (50 mmol) is dissolved in tetrahydrofuran (200 mL). The reaction is chilled to −78° C. under an inert atmosphere. A solution of n-butyllithium in hexanes (24 mL, 2.5M, 60 mmol) is added, and the reaction mixture is stirred for thirty minutes. A solution of oxirane dissolved in tetrahydrofuran (40 mL, 41.5M, 60 mmol) is added, and the reaction is allowed to warm to room temperature while stirring overnight. The solvent is removed under reduced pressure, and the crude material is dissolved in methylene chloride (200 mL) and washed with saturated ammonium chloride (2×50 mL), dried with sodium sulfate, and evaporated to dryness. The compound is purified by column chromatography to give 3-(4-chloro-6-morpholin-4-yl-pyrid-2-yl)-propan-1-ol.

Workup

additionis added
temperatureto warm to room temperature
stirringwhile stirring overnight
customThe solvent is removed under reduced pressure
dissolutionthe crude material is dissolved in methylene chloride (200 mL)
washwashed with saturated ammonium chloride (2×50 mL)
dry with materialdried with sodium sulfate
customevaporated to dryness
customThe compound is purified by column chromatography

Sources & evidence

ORD record: ord-e7a53f6e86d348988e18c0437946a856
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07872005B2

Reaction notes

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