Ethyl Acetate → HCID 86635761, compound

HRID 1630451Notes

Reaction equation

HRID 1630451 reaction equation
[C:1]([O:4][CH2:5][C:6](=O)[CH2:7][O:8][C:9](=[O:11])[CH3:10])(=[O:3])[CH3:2].Cl.[CH3:14][NH:15][CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CCOC(C)=O>ClC(Cl)C>[C:9]([O:8][CH2:7][CH:6]([N:15]([CH3:14])[CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:5][O:4][C:1](=[O:3])[CH3:2])(=[O:11])[CH3:10]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 2434181,3-DiacetoxyacetoneHCID 5049666Sodium triacetoxyborohydrideHCID 11252350Sarcosine t-butyl ester hydrochloride

Product 1

HCID 86635761HCID 86635761, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 3-(acetyloxy)-2-oxopropyl acetate (4.54 g, 26 mmol) in dichloroethane (75 ml) was added tert-butyl 2-(methylamino)acetate HCl. After stirring for 10 minutes sodium triacetoxyborohydride (8.3 g, 39 mmol) was added and stirring was continued for 18 hours and monitored by TLC (1:1heptane:EtOAc). The reaction was quenched by the addition of saturated sodium hydrogen carbonate solution and the crude product was extracted into dichloromethane. The organic phase was separated, dried over MgSO4, filtered and concentrated in vacuo. The title compound was purified by silica column chromatography eluting with 0-20% EtOAc:Hept to yield the title compound (1.32 g, 17% yield). 1H NMR (250 MHz, CHLOROFORM-d) δ 4.07-4.33 (4H, m), 3.34 (2H, s), 3.23 (1H, t, 5.9 Hz), 2.49 (3H, s), 1.99-2.19 (6H, m), 1.33-1.55 (9H, m).

Workup

  1. additionwas added
  2. customThe reaction was quenched by the addition of saturated sodium hydrogen carbonate solution
  3. extractionthe crude product was extracted into dichloromethane
  4. customThe organic phase was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe title compound was purified by silica column chromatography
  9. washeluting with 0-20% EtOAc

Sources & evidence

ORD record
ord-3ad16382816a42a5876e9868cfdc016f
Source dataset
uspto-grants-2014_07
Patent number
US08791134B2

Reaction notes

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