Methyl acetoacetate → HCID 18914303, compound

HRID 1292119Notes

Reaction equation

HRID 1292119 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[CH2:9]([NH2:12])[CH2:10][CH3:11].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl.C(O)(=O)C.ClCCCl>[CH2:9]([NH:12][CH:2]([CH2:3][CH3:5])[C:1]([O:7][CH3:8])=[O:6])[CH2:10][CH3:11]

Participants

8

Reactant 4

HCID 7757Methyl acetoacetateHCID 7852PropylamineHCID 10340Sodium CarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 18914303HCID 18914303, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 6 g of methyl acetoacetate, 5 mL of 1-propylamine, 40 mL of 1,2-dichloroethane, 3 mL of glacial acetic acid and 16 g of sodium triacetoxyborohydride was stirred at room temperature for 4 days. The reaction mixture was poured into 200 mL chloroform and 50 mL saturated aqueous Na2CO3 and the layers separated. The aqueous layer was extracted with 200 mL of chloroform and the combined organic layers dried over MgSO4 and concentrated under reduced pressure. After drying under vacuum, 9 g of (±)-methyl 2-(1-propylamino)butyrate was obtained as an oil: TLC (EtOAc); 1H NMR (400 MHz, CDCl3) 6.2 (br s, 1H), 3.65 (s, 3H), 3.2 (complex m, 2H), 2.65 (complex m, 2H), 2.45 (dd, 1H), 1.55 (m, 2H), 1.4 (d, 3H), 0.95 (t, 3H).

Workup

  1. customthe layers separated
  2. extractionThe aqueous layer was extracted with 200 mL of chloroform
  3. dry with materialthe combined organic layers dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customAfter drying under vacuum

Sources & evidence

ORD record
ord-2f197b074e014375a4ea5dffcb324e6f
Source dataset
uspto-grants-1998_05
Patent number
US05756508

Reaction notes

Loading…