Methyl 4-oxobutyrate → Methyl 4-(benzyl(1-ethoxy-1-oxopropan-2-yl)amino)butanoate

HRID 510236Notes

Reaction equation

HRID 510236 reaction equation
[CH2:1]([NH:8][CH:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][O:17][C:18](=[O:23])[CH2:19][CH2:20][CH:21]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[CH2:1]([N:8]([CH:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:21][CH2:20][CH2:19][C:18]([O:17][CH3:16])=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 83779Methyl 4-oxobutyrateHCID 222273Ethyl 2-(benzylamino)propanoateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 67423852Methyl 4-(benzyl(1-ethoxy-1-oxopropan-2-yl)amino)butanoateYield 95%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of the product of Example 112, step a (794 mg, 3.8 mmol) in DCE (10 mL) was added methyl-4-oxobutanoate (0.891 mL, 7.7 mmol) followed by Na(OAc)3BH (1.6 g, 7.7 mmol). The mixture was stirred at room temperature overnight and then quenched by the addition of saturated aqueous NaHCO3 solution. The layers were separated and the combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. Chromatography on SiO2 column eluting with EtOAc/Hex afforded the desired compound as a colorless liquid (1.11 g, 95%). MS (ESI) mass calcd. C17H25NO4, 307.2. m/z found 308.2 [M+H]+. 1H NMR (500 MHz, CDCl3) δ 7.35-7.20 (m, 5H), 4.22-4.12 (m, 2H), 3.86-3.80 (m, 1H), 3.67-3.60 (m, 4H), 3.52-3.45 (m, 1H), 2.69-2.56 (m, 2H), 2.41-2.26 (m, 2H), 1.80-1.71 (m, 2H), 1.33-1.24 (m, 6H).

Workup

  1. customquenched by the addition of saturated aqueous NaHCO3 solution
  2. customThe layers were separated
  3. dry with materialthe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washChromatography on SiO2 column eluting with EtOAc/Hex

Sources & evidence

ORD record
ord-47da825ff0284c208f66420b464f84ac
Source dataset
uspto-grants-2015_08
Patent number
US09096596B2

Reaction notes

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