Dichloromethane → methyl 8-(1-hydroxyethyl)-2-((R)-2-methylmorpholino)-4-oxo-4H-chromene-6-carboxylate

HRID 572804Notes

Reaction equation

HRID 572804 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:22]([O:24][CH3:25])=[O:23])[CH:7]=[C:8]2[C:13]=1[O:12][C:11]([N:14]1[CH2:19][CH2:18][O:17][C@H:16]([CH3:20])[CH2:15]1)=[CH:10][C:9]2=[O:21])(=[O:3])[CH3:2].C(Cl)Cl.[BH4-].[Na+]>CO>[OH:3][CH:1]([C:4]1[CH:5]=[C:6]([C:22]([O:24][CH3:25])=[O:23])[CH:7]=[C:8]2[C:13]=1[O:12][C:11]([N:14]1[CH2:19][CH2:18][O:17][C@H:16]([CH3:20])[CH2:15]1)=[CH:10][C:9]2=[O:21])[CH3:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 58235010methyl 8-acetyl-2-((R)-2-methylmorpholino)-4-oxo-4H-chromene-6-carboxylate

Product 1

HCID 58234968methyl 8-(1-hydroxyethyl)-2-((R)-2-methylmorpholino)-4-oxo-4H-chromene-6-carboxylateYield 86.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 8-acetyl-2-((R)-2-methylmorpholino)-4-oxo-4H-chromene-6-carboxylate (1.15 g, 3.33 mmol) in MeOH (20 mL)/DCM (10 mL) was added sodium tetrahydroborate (0.139 g, 3.66 mmol) at −10° C. The reaction mixture was quenched with water (50 mL) 15 min later. The volatiles were removed and the aqueous layer was extracted twice with DCM. Combined organics phases were washed with brine, dried over magnesium sulfate and concentrated. The residue was triturated with MTBE/DCM (9/1) and collected by filtration to give methyl 8-(1-hydroxyethyl)-2-((R)-2-methylmorpholino)-4-oxo-4H-chromene-6-carboxylate (1.0 g, 86%) as a grey solid, which was used in the next step without further purification. Mass Spectrum: M+H+ 348.

Workup

  1. customThe reaction mixture was quenched with water (50 mL) 15 min later
  2. customThe volatiles were removed
  3. extractionthe aqueous layer was extracted twice with DCM
  4. washCombined organics phases were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was triturated with MTBE/DCM (9/1)
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-b9fbb91e2099431784420d1677b98976
Source dataset
uspto-grants-2015_05
Patent number
US09029374B2

Reaction notes

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