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

HRID 1947365
Notes
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Reaction equation

HRID 1947365 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 887
Methanol
Solvent

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-0600238db363495ca888a765514e6622
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08399460B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes