Sodium borohydride → methyl 8-(1-hydroxyethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylate

HRID 1947289Notes

Reaction equation

[BH4-].[Na+].[C:3]([C:6]1[CH:7]=[C:8]([C:23]([O:25][CH3:26])=[O:24])[CH:9]=[C:10]2[C:15]=1[O:14][C:13]([N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)=[CH:12][C:11]2=[O:22])(=[O:5])[CH3:4]>CO.C(Cl)Cl>[OH:5][CH:3]([C:6]1[CH:7]=[C:8]([C:23]([O:25][CH3:26])=[O:24])[CH:9]=[C:10]2[C:15]=1[O:14][C:13]([N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)=[CH:12][C:11]2=[O:22])[CH3:4]

Participants

Conditions

Temperature: -10 °C

Procedure

Sodium tetrahydroborate (82 mg, 2.16 mmol) was added to a solution of methyl 8-acetyl-2-morpholino-4-oxo-4H-chromene-6-carboxylate (650 mg, 1.96 mmol) in methanol (20 mL) and DCM (10 mL) at −10° C. After 15 min of stirring at −10° C., the reaction mixture was quenched with water (25 mL). The volatiles were removed and the aqueous layer extracted twice with DCM. The combined organics phases were washed with brine, dried over magnesium sulfate and concentrated. The residue was triturated with diethylether and the solid collected by filtration to give methyl 8-(1-hydroxyethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylate (500 mg, 76%) as a brown solid, which used for the next step without further purification. Mass Spectrum: M+H+ 334.

Workup

customthe reaction mixture was quenched with water (25 mL)
customThe volatiles were removed
extractionthe aqueous layer extracted twice with DCM
washThe combined organics phases were washed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated
customThe residue was triturated with diethylether
filtrationthe solid collected by filtration

Sources & evidence

ORD record: ord-7769bbeb366640a5bac4a702e3c4a229
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399460B2

Reaction notes

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