Sodium Bicarbonate → HCID 67033256, compound

HRID 920586Notes

Reaction equation

HRID 920586 reaction equation
[CH3:1][O:2][C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH:5]=O.[Cl:10][C:11]1[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[C:12]=1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]2[O:26][CH2:25][CH2:24][NH:23][CH2:22]2)=[CH:17][CH:16]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[CH3:1][O:2][C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][N:23]1[CH2:24][CH2:25][O:26][CH:21]([C:18]2[CH:19]=[CH:20][C:15]([O:14][CH2:13][C:12]3[C:11]([Cl:10])=[CH:30][CH:29]=[CH:28][C:27]=3[Cl:31])=[CH:16][CH:17]=2)[CH2:22]1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 11137194Methyl 2,2-dimethyl-3-oxopropanoateHCID 67032413HCID 67032413, compound

Product 1

HCID 67033256HCID 67033256, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 2,2-dimethyl-3-oxo-propionic acid methyl ester (WHSS0374-001) (0.90 g; 5.44 mmol) in 1,2-dichloroethane (20 mL) was added 2-[4-(2,6-dichloro-benzyloxy)-phenyl]-morpholine (0.91 g, 2.7 mmol) and NaBH(OAc)3 (1.62 g; 7.62 mmol). The resulting mixture was stirred overnight at RT, and subsequently treated with 5% aqueous NaHCO3 (10 mL) and extracted with CH2Cl2 (3×30 ml). The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, Et2O/hexanes 1:1) to afford 3-{2-[4-(2,6-dichloro-benzyloxy)-phenyl]-morpholin-4-yl}-2,2-dimethyl-propionic acid methyl ester (1.12 g) as a clear colourless oil. The required 2,2-dimethyl-3-oxo-propionic acid methyl ester was prepared as follows: To a solution of 2,2-dimethyl-3-hydroxypropionic acid methyl ester (10.00 g; 75.7 mmol) in CH2Cl2 (200 mL) was added pyridinium chloroformate (28.54 g; 132.4 mmol) in small portions, at 0° C. The reaction mixture was allowed to slowly warm to RT and stirred overnight. Subsequently, the mixture was diluted with CH2Cl2, filtered over kieselguhr, and concentrated in vacuo. The remaining oil was purified by column chromatography (SiO2, hexanes/Et2O 7:3) to afford 2,2-dimethyl-3-oxo-propionic acid methyl ester (5.59 g)

Workup

  1. extractionextracted with CH2Cl2 (3×30 ml)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (SiO2, Et2O/hexanes 1:1)

Sources & evidence

ORD record
ord-e71df70fc1ca4d26b080ef628511b864
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Reaction notes

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