Tert-butyl acetoacetate → HCID 66653775, compound

HRID 571794Notes

Reaction equation

HRID 571794 reaction equation
[CH3:1][C:2]1[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[O:16][CH2:15][CH2:14][NH:13][CH2:12]2)=[CH:7][CH:6]=1.[C:22]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])(=[O:27])[CH2:23][C:24]([CH3:26])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl.C(O)(=O)C>[C:29]([O:28][C:22](=[O:27])[CH2:23][CH:24]([N:13]1[CH2:14][CH2:15][O:16][CH:11]([C:8]2[CH:7]=[CH:6][C:5]([O:4][C:3]3[CH:17]=[CH:18][CH:19]=[C:20]([CH3:21])[C:2]=3[CH3:1])=[CH:10][CH:9]=2)[CH2:12]1)[CH3:26])([CH3:32])([CH3:31])[CH3:30]

Participants

7

Reactant 4

HCID 15538Tert-butyl acetoacetateHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 66653665HCID 66653665, compound

Product 1

HCID 66653775HCID 66653775, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolvent

Procedure

A mixture of 2-[4-(2,3-dimethyl-phenoxy)-phenyl]-morpholine (1.00 g; 3.13 mmol), tert-butyl acetoacetate (2.07 mL; 12.5 mmol), sodium triacetoxyborohydride (1.86 g; 8.75 mmol), and a drop of acetic acid, in 1,2-dichloroethane (20 mL) was stirred overnight, at RT. The resulting mixture was treated with 5% aqueous NaHCO3 and extracted with CH2Cl2. The combined organic layers were dried (Na2SO4), filtered, concentrated in vacuo, and purified by column chromatography (SiO2, Et2O/hexanes 1:3) to afford 3-{2-[4-(2,3-dimethyl-phenoxy)-phenyl]-morpholin-4-yl}-butyric acid tert-butyl ester (1.17 g

Workup

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

Sources & evidence

ORD record
ord-43df0ab42c984001be4c3d69b663cd4a
Source dataset
uspto-grants-2015_05
Patent number
US09029371B2

Reaction notes

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