Ammonium Chloride → [6-Chloro-2-(morpholin-4-ylmethyl)pyridin-3-yl]methanol

HRID 385953Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[C:5]([C:15](OC)=[O:16])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH4+].[Cl-]>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[C:5]([CH2:15][OH:16])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Methyl 6-chloro-2-(morpholin-4-ylmethyl)pyridine-3-carboxylate (0.5 g, 1.847 mmol) was take up in THF (9 mL) and cooled to 0° C. LiAlH4, 2 M in THF (1.847 mL, 3.69 mmol) was added dropwise and the resulting mixture maintained at 0° C. for 5 hours. Saturated aqueous NH4Cl was added and the products extracted into EtOAc (3×). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Purification of the residue by silica gel chromatography (12-100% EtOAc-hexanes followed by 0-10% MeOH-EtOAc) gave the title compound as a pale yellow oil.

Workup

temperaturethe resulting mixture maintained at 0° C. for 5 hours
extractionthe products extracted into EtOAc (3×)
washThe combined organic extracts were washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customPurification of the residue by silica gel chromatography (12-100% EtOAc-hexanes followed by 0-10% MeOH-EtOAc)

Sources & evidence

ORD record: ord-792f3ba51f47436aa570135c33c7cd88
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367706B2

Reaction notes

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