Sodium Sulfate → [2-(Morpholin-4-yl)-1,3-thiazol-4-yl]methanol

HRID 625098Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[S:8][CH:9]=[C:10]([C:12](OC)=[O:13])[N:11]=2)[CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[O-]S([O-])(=O)=O.[Na+].[Na+]>C(OCC)C.C(OCC)(=O)C>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[S:8][CH:9]=[C:10]([CH2:12][OH:13])[N:11]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of methyl 2-morpholinothiazole-4-carboxylate (0.76 g, 3.33 mmol) in ethyl ether (20 mL) was treated portion wise over 10 min. with lithium aluminum hydride (0.38 g, 10.01 mmol). The mixture was stirred at −78° C. for 4 hours, then slowly treated with ethyl acetate (10 mL) and sat. Na2SO4 (20 mL). The mixture was allowed to warm up to RT, diluted with ethyl acetate, washed with sat. NaHCO3 (1×), brine (1×), dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified on silica gel chromatography (3×10 cm, 25% AcOEt/CH2Cl2 to 100% AcOEt) to give the title material as a beige solid (0.458 g) which was then distilled (bulb to bulb, 135-145° C./0.2 torr) and afforded the desired product (0.455 g, 68%) as a white solid. LC (Method F): 0.873 min. HRMS (ESI) calcd for C8H13N2O2S [M+H]+ m/z 201.07, found 201.2. 1H NMR (CDCl3, 400 MHz) δ ppm: 6.43 (s, 1H) 4.53 (d, J=3.9 Hz, 2H) 3.79 (m, 4H) 3.44 (m, 4H) 2.17 (s, 1H).

Workup

temperatureto warm up to RT
washwashed with sat. NaHCO3 (1×), brine (1×)
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified on silica gel chromatography (3×10 cm, 25% AcOEt/CH2Cl2 to 100% AcOEt)

Sources & evidence

ORD record: ord-4e520147885645179e1655baf731af75
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303065B2

Reaction notes

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